[ CAS No. 100622-34-2 ] {[proInfo.proName]}

Name: 100622-34-2|9-Anthraceneboronic acid|98%
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2D 3D

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Quality Control of [ 100622-34-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100622-34-2 ]

SDS Specification

Alternatived Products of [ 100622-34-2 ]

Product Details of [ 100622-34-2 ]

CAS No. :	100622-34-2	MDL No. :	MFCD03425925
Formula :	C₁₄H₁₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHHDLIWHHXBLBK-UHFFFAOYSA-N
M.W :	222.05	Pubchem ID :	15510213
Synonyms :

Calculated chemistry of [ 100622-34-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	71.28
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.33
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	2.26
Log Po/w (SILICOS-IT) :	1.39
Consensus Log Po/w :	1.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.86
Solubility :	0.0308 mg/ml ; 0.000139 mol/l
Class :	Soluble
Log S (Ali) :	-3.86
Solubility :	0.0309 mg/ml ; 0.000139 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.65
Solubility :	0.00501 mg/ml ; 0.0000225 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.98

Safety of [ 100622-34-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 100622-34-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 100622-34-2 ]
Downstream synthetic route of [ 100622-34-2 ]

[ 100622-34-2 ] Synthesis Path-Upstream 1~9

1
[ 150-46-9 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;	9-bromoanthracence (10.0 g, 38.9 mmol) was dissolvedin anhydrous THF solution (500 mL) and stirred at −78C. Then, 1.6 M n-BuLi (29.3 mL,46.7 mmol) was added. Triethyl borate (9.3 mL, 54.5 mmol) was added to the reaction after30 min. After the reaction was finished, the solution was acidified with 2 N HCl solutionat room temperature and extracted with ethyl acetate and water. The organic layer wasdried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue wasredissolved in hexane and added to ethyl acetate. The precipitate was filtered and washedwith hexane to obtain a beige compound (7.70 g, 89percent). 1H-NMR (300 MHz, CDCl3):δ(ppm) = 8.47 (s, 1H), 8.14 (d, J = 9.2 Hz, 2H), 8.04 (d, J = 9.8 Hz, 2H), 7.53–7.44 (m,4H), 5.07 (s, 2H).

Reference： [1] Journal of Materials Chemistry C, 2016, vol. 4, # 14, p. 2784 - 2792
[2] Journal of Materials Chemistry C, 2014, vol. 2, # 24, p. 4737 - 4747
[3] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
[4] Molecular Crystals and Liquid Crystals, 2007, vol. 471, # 1, p. 89 - 98
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 20, p. 5598 - 5602[6] Angew. Chem., 2017, vol. 129, # 20, p. 5690 - 5694,5
[7] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 8, p. 8854 - 8857
[8] Journal of Nanoscience and Nanotechnology, 2018, vol. 18, # 3, p. 2166 - 2170

2
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane; toluene at -40 - -10℃; for 0.5 h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane; toluene at -70 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene	9-Bromoanthracene 38.6 g was dissolved in dehydrated toluene 80 ml and dehydrated THF (tetrahydrofuran) 160 ml, and the solution was cooled to -40°C. A 1.58M n-butyllithium hexane solution 106 ml was dropwise added thereto and stirred at -40°C for 30 minutes, the temperature was elevated up to - 10°C. The solution was cooled again down to -70°C, and a dehydrated THF solution of trimethyl borate 50.0 ml was gradually dropwise added thereto. The solution was stirred at -70°C for 2 hours and then slowly heated up to room temperature. After left standing for a night, a 10 percent hydrochloric acid aqueous solution 100 ml was added thereto and stirred, and then it was extracted twice with toluene. The organic layer was washed with saturated brine and dried on anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from toluene/hexane, filtered and dried, whereby targeted 9-anthraceneboronic acid 24.4 g was obtained in the form of pale brown crystal (yield: 73 percent).

Reference： [1] New Journal of Chemistry, 2016, vol. 40, # 1, p. 58 - 62
[2] Patent: EP1707550, 2006, A1, . Location in patent: Page/Page column 34
[3] Journal of Materials Chemistry, 2008, vol. 18, # 28, p. 3376 - 3384
[4] Journal of Materials Chemistry, 2011, vol. 21, # 9, p. 2957 - 2964
[5] Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4856 - 4863
[6] Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4430 - 4441
[7] Journal of Organic Chemistry, 2004, vol. 69, # 3, p. 921 - 927
[8] Journal of Physical Chemistry A, 2000, vol. 104, # 6, p. 1130 - 1140
[9] Patent: WO2006/66126, 2006, A2, . Location in patent: Page/Page column 76-77
[10] Patent: US2002/19527, 2002, A1,
[11] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
[12] Journal of Nanoscience and Nanotechnology, 2015, vol. 15, # 7, p. 5438 - 5441

3
[ 121-43-7 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere Stage #2: at -78 - 20℃; Inert atmosphere	(i) 9-anthrylboronic acid A synthesis scheme of 9-anthrylboronic acid is shown in (C-1). In a 500 mL three-neck flask, 7.7 g (30 mmol) of 9-bromoanthracene was placed, and the air in the flask was replaced with nitrogen. Then, 200 mL of THF was added into the flask and the solution was cooled to -80° C. under nitrogen stream. After cooling, 18 mL (30 mmol) of 1.6 M n-butyllithium was dripped into the solution and stirred at the same temperature for 2 hours. After a certain period, 6.8 mL (60 mmol) of trimethyl borate was added into the solution, the temperature of the solution was raised to room temperature, and then, the solution was stirred for 17 hours. After a certain period, 100 mL of 1.0 M hydrochloric acid was added to the solution and stirred for 1 hour. An aqueous layer of the obtained mixture was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with saturated saline, and then the organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene, so that 5.2 g of target white powder was obtained in a yield of 80percent.

Reference： [1] Patent: US2009/286985, 2009, A1, . Location in patent: Page/Page column 65
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13052 - 13055[3] Angew. Chem., 2016, p. 13052 - 13055,4
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 7, p. 1201 - 1207
[5] Patent: US2010/190994, 2010, A1, . Location in patent: Page/Page column 23
[6] Patent: US2011/152587, 2011, A1, . Location in patent: Page/Page column 12
[7] Patent: US2018/114914, 2018, A1,

4
[ 150-46-9 ]
[ 1564-64-3 ]
[ 7732-18-5 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere Stage #2: at -78℃; Inert atmosphere Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; Inert atmosphere	As shown in Reaction Scheme 3 9-Bromoanthracene (10 g, 38.9 mmol) was added to a solution of Placed in a 3-neck round bottom flask and 300 mL of anhydrous THF under nitrogen. 2M n-BuLi (24.0 mL, 46.7 mmol) was slowly added while maintaining the temperature at -78 dege C. In the middle of the reaction, TLC was taken under the condition of EA: hexane = 1: 10, and the progress of the reaction was examined. After the spot of the reaction disappeared, triethyl borate (9.50 mL, 54.5 mmol) was added to -78 deg. The progress of the reaction was examined by taking TLC under the conditions of EA: hexane = 1: 10. After the reaction was completed, HCl (7.20 mL, 85.6 mmol) was added at room temperature, EA and H2O. A small amount of H2O in the EA layer was removed with MgSO4. After the MgSO4 was filtered off, the product in the EA layer was evaporated. The product was dissolved in a small amount of THF and reprecipitated with hexane, followed by filtration to obtain 7.55 g (yield 87percent) of Compound 6 as an orange solid.

Reference： [1] Patent: KR2016/39492, 2016, A, . Location in patent: Paragraph 0103-0107

5
[ 5419-55-6 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexanes at -20 - 18℃; for 1 h;	Compound 42d.; Step a: Preparation of 9-anthracene boronic acid; A solution of 9-bromoanthracene (1 g, 3.9 mmol) and triisopropylborate (1.35 ml, 5.85 mmol) in absolute THF (30 ml) was cooled down to -78°C and stirred under argon. roe-BuLi (2.9 ml, 1.6 M in hexanes, 4.68 mmol) was then added dropwise over one hour and it was stirred at -78° C for one hour. It was then warmed up to -20⁰C and2 M HCl (20 ml) was added. The mixture was warmed up to 18°C and stirred for one hour. The contents were diluted with diethyl ether (300 ml) and it was washed with water (2 x 100 ml) then with a saturated aqueous NaCl solution (50 ml). It was then dried over MgSO₄, filtered, and the solvent was removed under reduced pressure to afford a yellow solid. The solid was triturated with hexane, decanted and the supernatant solvent was removed with a pipette to give the desired boronic acid (588 mg, 68percent) as a pale yellow solid which was used in the next step without further purification.

Reference： [1] Patent: WO2006/135973, 2006, A1, . Location in patent: Page/Page column 30

6
[ 1028205-77-7 ]
[ 100622-34-2 ]

Reference： [1] Journal of Physical Chemistry A, 2000, vol. 104, # 6, p. 1130 - 1140
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 7, p. 1201 - 1207
[3] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571

7
[ 7647-01-0 ]
[ 121-43-7 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Reference： [1] Inorganic Chemistry, 2013, vol. 52, # 15, p. 8579 - 8590

8
[ 7732-18-5 ]
[ 1028205-77-7 ]
[ 100622-34-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 7, p. 1201 - 1207

9
[ 124108-68-5 ]
[ 100622-34-2 ]

Reference： [1] Ohio Journal of Science, 1958, vol. 58, p. 141,142
[2] Ohio Journal of Science, 1958, vol. 58, p. 141,142

[ 100622-34-2 ] Synthesis Path-Downstream 1~88

1
[ 1714-29-0 ]
[ 100622-34-2 ]
1-(anthracen-9-yl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; toluene;Reflux;	2 L round bottom flask85 g (302 mmol) of 1-bromopyrene, 80.6 g (363 mmol) of 9-anthraceneboronic acid, 2.4 g (15 mmol) of tetrakis (triphenylphosphine) palladium (0), 83.6 g of potassium carbonate (605 mmol), 425 mL of 1,4-dioxane, 425 mL of toluene, and 170 mL of water were added and refluxed with stirring. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate / water, the organic layers were collected, concentrated, recrystallized with methylene chloride / methanol, and dried by filtration. (96 g, 83.5%)
50%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	The reaction vessel was charged with 9-A (7.88 g, 35.50 mmol),1-bromopyrene (9.98 g, 35.50 mmol),Tetrakistriphenylphosphine palladium (1.4 g, 2.16 mmol),Potassium carbonate (10.6 g, 76.6 mmol),Toluene 220mL, ethanol 40mL and 40mL of distilled water after stirring at 120 for 3h.After completion of the reaction, the reaction mixture was quenched with ethyl acetate.The organic layer is dried over MgSO4.The solvent was distilled off under reduced pressure and then purified on a silica gel column to give Compound 9-B (6.72 g, 50%).

Reference： [1]Patent: KR102017506,2019,B1 .Location in patent: Paragraph 0224; 0228-0230
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 4737 - 4747
[3]Patent: CN107382748,2017,A .Location in patent: Paragraph 0050; 0054; 0055; 0056
[4]Journal of Physical Chemistry A,2000,vol. 104,p. 1130 - 1140

2
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
73%		9-Bromoanthracene 38.6 g was dissolved in dehydrated toluene 80 ml and dehydrated THF (tetrahydrofuran) 160 ml, and the solution was cooled to -40C. A 1.58M n-butyllithium hexane solution 106 ml was dropwise added thereto and stirred at -40C for 30 minutes, the temperature was elevated up to - 10C. The solution was cooled again down to -70C, and a dehydrated THF solution of trimethyl borate 50.0 ml was gradually dropwise added thereto. The solution was stirred at -70C for 2 hours and then slowly heated up to room temperature. After left standing for a night, a 10 % hydrochloric acid aqueous solution 100 ml was added thereto and stirred, and then it was extracted twice with toluene. The organic layer was washed with saturated brine and dried on anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from toluene/hexane, filtered and dried, whereby targeted 9-anthraceneboronic acid 24.4 g was obtained in the form of pale brown crystal (yield: 73 %).
		Scheme Dl; [00314] sec-BuLi (4.3 mL, 6.0 mmol, 1.4M solution in cyclohexane) was added dropwise to a solution of 9-bromoanthracene (1.29 g, 5.0 mmol) in Et2O (20 mL) at OC under N2. The reaction was held at OC for 15 minutes then warmed to rt and stirred an additional 45 minutes. Triisopropylborate (1.5 mL, 6.5 mmol) was added and the reaction was stirred at rt for 18h. Concentrated HCl (1.0 mL) and MeOH (1.0 mL) was added and the reaction was stirred for 30 minutes. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers EPO <DP n="79"/>were washed with H2O, sat. NaHCO3 (aq.), brine, and then dried over Na2SO4. Filtration and concentration gave 1.05 g of 9-anthraceneboronic acid.[00315] A reaction flask was charged, under N2, with 9-anthraceneboronic acid(220 mg, 1.0 mmol), Pd(PPh3)4 (29 mg, 5.0 mol%), 2,4-dibromothiazole (122 mg, 0.5 mmol), Na2CO3 (0.5 mL, 2.0 M solution in H2O), and toluene (4.0 mL). The reaction was heated at 9OC for 18h. After cooling to rt, water was added and the layers were separated. The aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with H2O, brine, and then dried over Na2SO4. The crude product mixture was purified by silica gel chromatography eiuting with 1% Et2O in hexanes. Isolated 93 mg, 50% yield, of 2-anthracenyl-4-bromothiazole.
	In ethyl acetate;	EXAMPLE 7A 9-anthrylboronic acid The desired product was prepared by substituting 9-bromoanthracene for 3-bromo-1,1'-biphenyl in Example 6A, and purified by flash column chromatography on silica gel with 9:1/hexanes:ethyl acetate to 7:3/hexanes:ethyl acetate. MS (DCI/NH3) m/z 268 (M+2NH4)+.

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 58 - 62
[2]Patent: EP1707550,2006,A1 .Location in patent: Page/Page column 34
[3]Journal of Materials Chemistry,2008,vol. 18,p. 3376 - 3384
[4]Journal of Materials Chemistry,2011,vol. 21,p. 2957 - 2964
[5]Journal of Organic Chemistry,2007,vol. 72,p. 4856 - 4863
[6]Chemistry - A European Journal,2003,vol. 9,p. 4430 - 4441
[7]Journal of Organic Chemistry,2004,vol. 69,p. 921 - 927
[8]Journal of Physical Chemistry A,2000,vol. 104,p. 1130 - 1140
[9]Patent: WO2006/66126,2006,A2 .Location in patent: Page/Page column 76-77
[10]Patent: US2002/19527,2002,A1
[11]Chemistry - A European Journal,2013,vol. 19,p. 15565 - 15571
[12]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5438 - 5441

3
[ 150-46-9 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
89%		9-bromoanthracence (10.0 g, 38.9 mmol) was dissolvedin anhydrous THF solution (500 mL) and stirred at -78C. Then, 1.6 M n-BuLi (29.3 mL,46.7 mmol) was added. Triethyl borate (9.3 mL, 54.5 mmol) was added to the reaction after30 min. After the reaction was finished, the solution was acidified with 2 N HCl solutionat room temperature and extracted with ethyl acetate and water. The organic layer wasdried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue wasredissolved in hexane and added to ethyl acetate. The precipitate was filtered and washedwith hexane to obtain a beige compound (7.70 g, 89%). 1H-NMR (300 MHz, CDCl3):delta(ppm) = 8.47 (s, 1H), 8.14 (d, J = 9.2 Hz, 2H), 8.04 (d, J = 9.8 Hz, 2H), 7.53-7.44 (m,4H), 5.07 (s, 2H).

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2784 - 2792
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 4737 - 4747
[3]Molecular Crystals and Liquid Crystals,2015,vol. 618,p. 47 - 54
[4]Molecular Crystals and Liquid Crystals,2007,vol. 471,p. 89 - 98
[5]Angewandte Chemie - International Edition,2017,vol. 56,p. 5598 - 5602
Angew. Chem.,2017,vol. 129,p. 5690 - 5694,5
[6]Journal of Nanoscience and Nanotechnology,2016,vol. 16,p. 8854 - 8857

4
[ 626-39-1 ]
[ 100622-34-2 ]
[ 713542-04-2 ]

Yield	Reaction Conditions	Operation in experiment
		(Example 2); (Method of producing Exemplified Compounds Nos. 35 and 60); Pd (PPh3) a Br ; BtOH2 Na2C03 aq. i i i Br Br toluene/ETOH-CHC13 Me Me Me Mu i... Br HN : i i i l r i I 4 ff il¢tr3 Pd (dba) 2/P (tBu) 3 BrrS) rirBr TITY tBuONa xylene (1w (Synthesis of Intermediate (IV)) In a stream of nitrogen, 25.8 g (82 mmol) of tribromobenzene and 109.5 g (0.491 mol) of <strong>[100622-34-2]anthracene-9-boronic acid</strong> were dissolved in a deaerated mixture solvent of 1 1 of toluene and 500 ML of ethanol and then the whole was stirred. A sodium carbonate aqueous solution prepared by dissolving 86. 8 g of anhydrous sodium carbonate in 800 ml of water was added dropwise into the solution. In a stream of nitrogen, the resulting mixture was stirred for 1 hour in an oil bath heated to 80C, followed by the addition of 14.2 g (12.3 mmol) of tetrakis (triphenylphosphine) palladium. Then, the mixture was heated and stirred for about 4 hours in an oil bath heated to 80C. The temperature of the reaction solution was returned to room temperature and further cooled to 5C, followed by filtering the precipitated crystal out. The crystal was dissolved in a mixture solvent of chlorobenzene and heptane under heating and then purified by silica gel column chromatography (CHLOROBENZENE : heptane = 1 : 3), resulting in 25 g of Intermediate (III).

Reference： [1]Patent: WO2005/787,2005,A1 .Location in patent: Page 49-50
[2]Journal of the American Chemical Society,2017,vol. 139,p. 13349 - 13360

5
[ 100622-34-2 ]
[ 5021-45-4 ]
2-(4-anthracen-9-yl-phenyl)-quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux;	Two grams (7.0 mmol) of 4-(4-bromo-phenyl)-quinoxaline obtained in the above step (1), 1.7 g (7.7 mmol) of 9-anthratheneboronic acid and 0.16 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 12 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 2.37 g of 2-(4-anthracen-9-yl-phenyl)-quinoxaline (yield: 88 %).

Reference： [1]Patent: EP1582516,2005,A1 .Location in patent: Page/Page column 81

6
[ 100622-34-2 ]
[ 4175-77-3 ]
[ 893394-67-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 90℃; for 18h;	Scheme Dl; [00314] sec-BuLi (4.3 mL, 6.0 mmol, 1.4M solution in cyclohexane) was added dropwise to a solution of 9-bromoanthracene (1.29 g, 5.0 mmol) in Et2O (20 mL) at O°C under N2. The reaction was held at O°C for 15 minutes then warmed to rt and stirred an additional 45 minutes. Triisopropylborate (1.5 mL, 6.5 mmol) was added and the reaction was stirred at rt for 18h. Concentrated HCl (1.0 mL) and MeOH (1.0 mL) was added and the reaction was stirred for 30 minutes. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers EPO <DP n="79"/>were washed with H2O, sat. NaHCO3 (aq.), brine, and then dried over Na2SO4. Filtration and concentration gave 1.05 g of 9-anthraceneboronic acid.[00315] A reaction flask was charged, under N2, with 9-anthraceneboronic acid(220 mg, 1.0 mmol), Pd(PPh3)4 (29 mg, 5.0 molpercent), <strong>[4175-77-3]<strong>[4175-77-3]2,4-dibromothiazol</strong>e</strong> (122 mg, 0.5 mmol), Na2CO3 (0.5 mL, 2.0 M solution in H2O), and toluene (4.0 mL). The reaction was heated at 9O°C for 18h. After cooling to rt, water was added and the layers were separated. The aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with H2O, brine, and then dried over Na2SO4. The crude product mixture was purified by silica gel chromatography eiuting with 1percent Et2O in hexanes. Isolated 93 mg, 50percent yield, of 2-anthracenyl-4-bromothiazole.

Reference： [1]Patent: WO2006/66126,2006,A2 .Location in patent: Page/Page column 76-77

7
C₁₇H₂₂BrNOS [ No CAS ]
[ 100622-34-2 ]
C₃₁H₃₁NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃;	Scheme C4; [00309] A reaction flask was charged, under N2, with C24 (74 mg, 0.19 mmol),2,6-dichlorophenylboronic acid (57 mg, 0.30 mmol), CsF (35 mg, 0.23 mmol), Pd(tBu3P)2 (5 mol%), and dioxane (2 mL). The reaction was heated at 100C overnight. The crude reaction mixture was purified by silica gel chromatography eluting with 2% Et2O in hexanes. Isolated 54mg, 54% yield, of C14 as a light yellow solid. 1H NMR (300 MHz, CDCl3) delta 1.39 (s, 9H, 'Bu), 7.24-7.45 (m, 8H), 7.62-7.67 (m, 3H), 12.41 (s, 1H, OH). EPO <DP n="78"/>[00310] Ligands C18, C22, and C23 were synthesized as described for C14 in yields of 25%, 50%, and 37%, respectively.[00311] Ligands C17 and C19 were synthesized as described for C14 but usingPd(PPh3) 4, Na2CO3, and toluene. Yield of C17 was 60% and C19 was 54%.

Reference： [1]Patent: WO2006/66126,2006,A2 .Location in patent: Page/Page column 75-76

8
[ 22082-99-1 ]
[ 100622-34-2 ]
[ 866611-28-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 5h;Heating / reflux;	9-Anthraceneboronic acid 10.7 g, 2-(4-bromophenyl)naphthalene 11.3 g and tetrakis(triphenylphosphine)palladium 2.3 g were mixed and substituted with argon. DME (dimethoxyethane) 140 ml and a 2M sodium carbonate aqueous solution 60 ml were added thereto, and the mixture was heated and refluxed for 5 hours. After left cooling, the deposited crystal was filtered and washed with ethanol and toluene. The crystal thus obtained was recrystallized from toluene, filtered and dried, whereby targeted (9-(4-naphthalene-2-yl-phenyl)anthracene 13.25 g was obtained (yield: 87 %).

Reference： [1]Patent: EP1707550,2006,A1 .Location in patent: Page/Page column 34

9
[ 5419-55-6 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
68%		Compound 42d.; Step a: Preparation of 9-anthracene boronic acid; A solution of 9-bromoanthracene (1 g, 3.9 mmol) and triisopropylborate (1.35 ml, 5.85 mmol) in absolute THF (30 ml) was cooled down to -78C and stirred under argon. r°-BuLi (2.9 ml, 1.6 M in hexanes, 4.68 mmol) was then added dropwise over one hour and it was stirred at -78 C for one hour. It was then warmed up to -200C and2 M HCl (20 ml) was added. The mixture was warmed up to 18C and stirred for one hour. The contents were diluted with diethyl ether (300 ml) and it was washed with water (2 x 100 ml) then with a saturated aqueous NaCl solution (50 ml). It was then dried over MgSO4, filtered, and the solvent was removed under reduced pressure to afford a yellow solid. The solid was triturated with hexane, decanted and the supernatant solvent was removed with a pipette to give the desired boronic acid (588 mg, 68%) as a pale yellow solid which was used in the next step without further purification.

Reference： [1]Patent: WO2006/135973,2006,A1 .Location in patent: Page/Page column 30

10
[ 121-43-7 ]
[ 1564-64-3 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
80%		(i) 9-anthrylboronic acid A synthesis scheme of 9-anthrylboronic acid is shown in (C-1). In a 500 mL three-neck flask, 7.7 g (30 mmol) of 9-bromoanthracene was placed, and the air in the flask was replaced with nitrogen. Then, 200 mL of THF was added into the flask and the solution was cooled to -80 C. under nitrogen stream. After cooling, 18 mL (30 mmol) of 1.6 M n-butyllithium was dripped into the solution and stirred at the same temperature for 2 hours. After a certain period, 6.8 mL (60 mmol) of trimethyl borate was added into the solution, the temperature of the solution was raised to room temperature, and then, the solution was stirred for 17 hours. After a certain period, 100 mL of 1.0 M hydrochloric acid was added to the solution and stirred for 1 hour. An aqueous layer of the obtained mixture was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with saturated saline, and then the organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene, so that 5.2 g of target white powder was obtained in a yield of 80%.
80.6%		2 L round bottom flask100 g (389 mmol) of 9-bromoanthracene and 800 mL of tetrahydrofuran are added, cooled to -78 C while blowing nitrogen, and dissolved with stirring. 267.4 mL of 1.6 M n-BuLi was slowly dropped and stirred for 2 hours while maintaining the temperature, 65 mL of trimethylborate was dropped, the ice bath was removed, and the mixture was stirred at room temperature for one day.After the reaction was completed, 2M hydrochloric acid was added and stirred, followed by extraction with ethyl acetate and water.The crystals were caught with toluene, filtered and dried (69.6 g, 80.6%).
		Under nitrogen atmosphere, 9-bromoanthracene (20.0 g, 77.8 mmol) was dissolved in tetrahydrofuran (200 mL), and the solution was chilled to -78 C. To the solution, n-butyllithium (n-BuLi, 2.5M in hexane) (37.4 mL, 93.4 mmol) was slowly added dropwise. After 30 minutes, trimethylborate (17.7 mL, 155.6 mmol) was added dropwise thereto. The temperature was slowly raised, and the mixture was further stirred at room temperature for one day. To the mixture, 1N aqueous hydrochloric acid (200 mL) was added, and the resultant mixture was stirred for minutes, and extracted with water (300 mL) and dichloromethane (200 mL). The extract was dried under reduced pressure and recrystallized from ethyl acetate (30 mL) and hexane (500 mL) to obtain 9-anthraceneboronic acid (9.3 g, 41.9 mmol).

		Preparation Example 1; Preparation of Compound (101); Preparation of Compound (201); Under nitrogen atmosphere, 9-bromoanthracene (20.0 g, 77.8 mmol) was dissolved in tetrahydrofuran (200 mL), and the solution was chilled to -78 C. To the solution, slowly added dropwise was n-butyl lithium (n-BuLi, 2.5M in hexane) (37.4 mL, 93.4 mmol). After 30 minutes, trimethylborate (17.7 mL, 155.6 mmol) was added thereto, and the resultant mixture was warmed to room temperature. After stirring at the same temperature for one day, 1N aqueous hydrochloric acid solution (200 mL) was added. The mixture was stirred for 30 minutes, and extracted from water (300 mL) and dichloromethane (200 mL). The extract was dried under reduced pressure and recrystallized from ethyl acetate (30 mL) and hexane (500 mL) to obtain the objective compound (201) (9.3 g, 41.9 mmol).
	With hydrogenchloride; n-butyllithium;	2nd step: anthracene-9-ylboronic acid 9-bromoanthracene (20.0 g, 77.80 mmol, 1.0 eq) was dissolved in THF (400 mL), and the solution was cooled to -80 C. 40 mL n-butyl lithium solution (2.5M in hexane, 101.14 mmol, 1.3 eq) were added dropwise, and the mixture was stirred for 2 h at this temperature. Trimethylborate (31.5 mL, 233.40 mmol, 3.0 eq) was added and the reaction mixture was stirred overnight, while the temperature was allowed to slowly rise to RT. The reaction was quenched by addition of aqueous HCl (12.0 mL, 20 wt. %). After 30 min of stiffing, the mixture was extracted with dichloromethane and water. The combined organic phases were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure. The residue was then triturated in MeOH for 1 h, filtered and rinsed with MeOH. After drying overnight in vacuum at 40 C., 13.76 g (80%) yield of the purified intermediate was obtained. HPLC purity: 98.95%

Reference： [1]Patent: US2009/286985,2009,A1 .Location in patent: Page/Page column 65
[2]Patent: KR102017506,2019,B1 .Location in patent: Paragraph 0224; 0225-0227
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 13052 - 13055
Angew. Chem.,2016,p. 13052 - 13055,4
[4]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1201 - 1207
[5]Patent: US2010/190994,2010,A1 .Location in patent: Page/Page column 23
[6]Patent: US2011/152587,2011,A1 .Location in patent: Page/Page column 12
[7]Patent: US2018/114914,2018,A1

11
[ 626-55-1 ]
[ 100622-34-2 ]
[ 20308-97-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 7h;Inert atmosphere;	(ii) Synthesis of 3-(9-anthryl)pyridine A synthesis scheme of 3-(9-anthryl)pyridine is shown in (C-2). In a 200 mL three-neck flask, 5.2 g (23 mmol) of 9-anthrylboronic acid, 4.0 g (25 mmol) of 3-bromopyridine, 5.2 g (50 mmol) of sodium carbonate, 50 mL of toluene, 25 muL of ethanol, and 25 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 0.28 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80 C. for 7 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined, washed with saturated saline, and dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give an oily substance. The oily substance was recrystallized with toluene/hexane, so that 2.8 g of target yellow powder was obtained in a yield of 46%.

Reference： [1]Patent: US2009/286985,2009,A1 .Location in patent: Page/Page column 65

12
[ 57103-02-3 ]
[ 100622-34-2 ]
[ 1246891-45-1 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 7707 - 7719

13
[ 13720-06-4 ]
[ 100622-34-2 ]
[ 1062556-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 24h;	Preparation Example 13; Preparation of Compound (113); Preparation of Compound (250); In toluene (400 mL) and ethanol (200 mL), dissolved were <strong>[13720-06-4]2,6-dibromonaphthalene</strong> (10.0 g, 35.0 mmol), Compound (201) (17.1 g, 76.9 mmol) and tetrakispalladium (O) triphenylphosphine (Pd(PPh3)4) (4.0 g, 3.5 mmol). To the solution, aqueous 2M sodium carbonate solution (175 mL) was added, and the mixture was stirred at 120 C. under reflux for one day. Then, the mixture was cooled to 25 C., and the reaction was quenched by adding distilled water (500 mL). The reaction mixture was extracted with ethyl acetate (200 mL), and the extract was dried under reduced pressure. Recrystallization from tetrahydrofuran (50 mL) and methanol (500 mL) gave the objective compound (250) (13.7 g, 28.5 mmol).

Reference： [1]Patent: US2011/152587,2011,A1 .Location in patent: Page/Page column 28-29

14
[ 1319659-48-7 ]
[ 100622-34-2 ]
[ 1319659-49-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; In N,N-dimethyl-formamide; at 90℃; for 24h;Inert atmosphere;	A mixture of 4,6-bis(5-bromo-2-methoxyphenyl)-2-methylpyrimidine (465 mg, 1.0 mmol), 9-anthraceneboronic acid (888 mg, 4.0 mmol), potassium phosphate (1.27 g, 6.0 mmol), and bis(benzonitrile)palladium(II) dichloride (38 mg, 0.10 mmol) were added in DMF (25 mL) under argon atmosphere. Tri(tert-butyl)phosphine (0.90 mL, 3.7 mmol) was added to the solution and then the mixture was stirred at 90 oC for 24 h. After the mixture was cooled to room temperature, the separated solids were collected and washed with water (30 mL x 2), acetone (20 mL x 2), and dichloromethane (10 mL x 2), to give 1b (465 mg, 0.71 mmol, 71%) as white powder. Low solubility of 1b in common solvents, such as chloroform, DMSO, toluene, DMF and pyridine, prevents NMR measurement. IR (KBr disk, r.t.) nu 3050, 3025, 2961, 2930, 1676, 1605, 1561, 1524, 1501, 1269, 1242, 1146, 1022, 885, 818, 731 cm-1; Elemental Analysis: Calcd. for C47H34N2O2+0.5(H2O) C, 84.53; H, 5.28; N, 4.19. Found: C, 84.13; H, 5.13; N, 4.41.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 3883 - 3885

15
[ 100622-34-2 ]
[ 2620-76-0 ]
[ 944801-79-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Reflux; Inert atmosphere;	In the flask, 9-indoleboronic acid (5 g, 22 mmol) was added.<strong>[2620-76-0]2-(4-bromophenyl)-1-phenyl-1H-benzimidazole</strong> (7.9 g, 22 mmol),Potassium carbonate (6g, 44mmol),Tetrahydrofuran (100mL),Water (50mL),Tetrakistriphenylphosphine palladium (0.5g),Heated under nitrogen for 5 hours,cool down,The crude product was purified by column chromatography to give 7.1 g,The yield was 73%.

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 2957 - 2964
[2]Patent: CN108752317,2018,A .Location in patent: Paragraph 0054; 0055; 0056

16
[ 1124-08-9 ]
[ 100622-34-2 ]
[ 1401514-52-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide; In water; for 5h;Reflux;	General procedure: To a mixture of diarylhalide (1 mmol), aryl boronic acid (2.1 mmol), and NaOH (3 mmol) in 2 mL water, PNP-SSS catalyst (0.05 g) was added and heated in an oil bath at the refluxing temperature of water. The reaction was followed by TLC. After completion of the reaction, the mixture was cooled down to room temperature and filtered and the remaining solid was washed with dichloromethane (3 x 5 mL) in order to separate catalyst. After the extraction of dichloromethane from water, the organic extract was dried over Na2SO4. The products were purified by column chromatography (hexane or hexane/ethyl acetate) to obtain the desired purity.

Reference： [1]Journal of Organometallic Chemistry,2012,vol. 717,p. 141 - 146

17
[ 1147081-43-3 ]
[ 100622-34-2 ]
[ 1391996-94-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Inert atmosphere; Reflux; Darkness;	A 100 ml two-neck round-bottomed flask was added compound 1 (0.90 g, 2 mmol), anthracen-9-ylboronic acid (0.49 g, 2.2 mmol), toluene (30 ml), ethanol (15 ml), 2 M K2CO3 (30 ml, 60 mmol) aqueous solution and tetrakis-(triphenylphosphine) palladium (0) (0.12 g, 0.1 mmol) in turn, then the reaction mixture was refluxed under nitrogen for 24 h in the absence of light. After the reaction was completed, cooled to room temperature. The solution was extracted with dichloromethane, dried by MgSO4. The organic layer was concentrated under a reduced pressure and purified by column chromatography and dried under vacuum to yield a white solid. Yield: 90%. 1H-NMR: (DMSO-d6, 400 MHz): delta (ppm) 8.95 - 8.93 (d, J = 8.0 Hz, 1H), 8.90 - 8.88 (d, J = 8.0 Hz, 1H), 8.79 - 8.76 (d, J = 8.0 Hz, 1H), 8.66 (s, 1H), 8.15 - 8.12 (d, J = 8.0 Hz, 2H), 7.84 - 7.77 (m, 5H), 7.76 - 7.68 (m, 4H), 7.59 - 7.46 (m, 5H), 7.44 - 7.33 (m, 5H), 7.15 - 7.13 (d, J = 8.0 Hz, 1H). MS (APCI) (m/z): [M+H+] calcd for C41H27N2, 547.7; found, 547.2. 13C NMR (100 MHz, DMSO-d6) delta (ppm) 150.68, 139.14, 138.75, 137.10, 135.92, 131.31, 131.25, 130.90, 130.81, 130.14, 129.79, 129.69, 129.60, 129.65, 128.94, 128.40, 128.23, 128.00, 127.25, 127.14, 126.46, 126.27, 126.23, 125.80, 125.75, 125.00, 124.17, 123.00, 122.53, 120.72. Anal. Calcd for C41H26N2: C, 90.08; H, 4.79; N, 5.12. Found: C, 89.90; H, 4.89; N, 5.21.

Reference： [1]Organic electronics,2012,vol. 13,p. 3050 - 3059

18
[ 100622-34-2 ]
[ 140-29-4 ]
[ 1210-12-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tert.-butylhydroperoxide; copper(l) iodide; In N,N-dimethyl acetamide; water; at 130℃; for 20h;	General procedure: Boronic acid 1 (0.5mmol), benzyl cyanide 2 (0.75mmol), CuI (95mg, 0.5mmol), tert-BuOOH (70% aq, 144muL, 1mmol), and DMAc (2mL) were placed in a 25mL round flask. The reaction mixture was stirred at 130C (oil bath) for 20h under air. After cooling to the room temperature, the resulting mixture was poured to 15mL water and extracted with dichloromethane (3×5mL). The organic phase was combined and dried over anhydrous Na2SO4. Dichloromethane was evaporated under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the product 3.

Reference： [1]Tetrahedron,2013,vol. 69,p. 8400 - 8404

19
[ 100622-34-2 ]
[ 1122-91-4 ]
[ 169831-24-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere;	Compound P-formaldehyde (187.5 mg, 1 . 01mmol), 9-boric acid anthracene (150 mg, 0 . 68mmol), double (triphenylporphyrin phosphorus) palladium dichloride Pd (PPh3)2Cl2(23.72 mg, 0 . 034mmol), dissolved in 20 ml tetrahydrofuran mixed solvent of toluene and (Vtoluene: VTHF= 1:1) in, under the protection of nitrogen 90 C reflux reaction, thin-layer chromatography tracking to the reaction is complete. The solution obtained after the organic solvent, a revolving off, the extraction with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product using petroleum ether and ethyl acetate mixed solvent (20:1) column, to obtain 4 - (anthracene-9-yl) benzaldehyde (yellow crystalline solid, 311.2 mg, yield 90%).
21%	With palladium 10% on activated carbon; sodium carbonate; In ethanol; water; at 20℃; for 24h;Inert atmosphere;	A round-bottom flask was charged with 4-bromobenzaldehyde (3; 105 muL, 0.5 mmol, 1.0 eq), anthracen-9-ylboronic acid (4A;111 mg, 0.5 mmol, 1.0 eq), Na2CO3 (202 mg, 1.9 mmol, 3.8 eq), 10% Pd/C (20 mg,0.02 mmol, 0.04 eq), H2O (1 mL) and EtOH (1 mL). After three vacuum/argon cyclesto remove air from the reaction flask, the reaction mixture was stirred at roomtemperature under argon for 24 h. Then the mixture was diluted with H2O (10 mL) andAcOEt (10 mL), and filtered to remove Pd/C. The organic phase was separated, and the aqueous layer wasextracted with AcOEt (3 × 3 mL). The combined organic layers were washed with brine (10 mL) and dried(Na2SO4). The solvent was removed by evaporation in vacuo. The residue was purified by flash silica gel columnchromatography (silica gel 10 g, hexanes/ethyl acetate = 90/10), affording 4-(anthracen-9-yl)benzaldehyde (1bA;30 mg, 21% yield): Registry number 169831-24-7; Rf = 0.58 (hexane:AcOEt = 80:20); 1H NMR (300 MHz,CDCl3) delta 7.13-7.50 (m, 4H, Ar), 7.50-7.76 (m, 4H, Ar), 7.88-8.19 (m, 4H), 8.49 (s, 1H), 10.16 (s, 1H, -CHO); 13CNMR (75 MHz, CDCl3) delta 192.15 (C=O), 145.78 (C), 135.66 (C), 135.25 (C), 132.12 (CH), 131.27 (C), 129.80(CH), 129.76 (C), 128.54 (CH), 127.38 (CH), 126.14 (CH), 125.88 (CH), 125.27 (CH).

Reference： [1]Patent: CN105418515,2016,A .Location in patent: Paragraph 0123; 0124; 0125
[2]Organic Letters,2020,vol. 22,p. 4276 - 4282
[3]Tetrahedron Letters,2014,vol. 55,p. 1946 - 1948
[4]Chemistry - A European Journal,2018,vol. 24,p. 636 - 645

20
[ 1637596-58-7 ]
[ 100622-34-2 ]
[ 1637596-67-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; water; at 80℃;	General procedure: To a solution of pentacene 3g (1 equiv, ca. 0.1 mmol scale), the corresponding boronic acid (1.5 equiv) and Pd(PPh3)2Cl2 (5 mol%) in dry, deoxygenated THF (20 mL) was added aqueous Na2CO3 (2 equiv dissolved in 5 mL H2O). The resulting dark solution was heated at 80 C for 2-4 h. After cooling the mixture to rt, the solvent was removed and the resulting blue product purified column chromatography and then recrystallization as noted in the individual procedures, providing pentacenes 3j and 3k as deep blue solids.

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1692 - 1705

21
[ 1628735-11-4 ]
[ 100622-34-2 ]
[ 1616797-69-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In toluene; at 120℃; for 18h;	A solution of 3 (400 mg, 1.2 mmoi), <strong>[100622-34-2]anthracene-9-boronic acid</strong> (390 mg, 1.8tnmol), Pd(PPh3)4 (208 mg, 0.2 mmol), and K3P04 (636.8 mg, 3.0 mmol) in 15 niL of toluenewas stirred at 120 C for 18 hours. The resulting mixture was allowed to cool to room temperature, quenched with water, and extracted with CH2C12. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2CI2:hexanes 4:1) afforded 206 mg (0.5 mmol, 40% yield) of a yellow solid.?H NMR: 8 3.61 (s, 31-1), 5.53 (d, J = 8.5 Hz, IH), 6.30 (dd, J = 8.5 Hz, 2.2 Hz, 11-I), 6.63 (d,J 2.1 Hz, 1H), 7.08 (d,J 7.0 Hz, 1H), 7.20-7.41 (m, 7H), 7.49 (dd,J = 7.7 Hz,7.5 Hz, 1H), 7,63 (dd,J 7.8 Hz, 7.4 Hz, 1H),7.78 (d,J 8.5 Hz, 1H), 7.84 (d,J 8.5 Hz, 1H),8.05-8.08 (m, 2H), 8.11 (d,J 8.2 Hz, 1H), 9.63 (a, lIt). 13C NMR: 8 = 55.3, 108,0, 121.4, 124.7,125.0, 125.1, 125.3, 125.4, 125.7, 125.9, 126.9, 127.1, 127.7, 127.8, 127.9, 129.2, 129.4, 130.0,130.7, 130.9, 131.2, 131.3, 131.8, 132.0, 133.8, 134.7, 135.0, 135.6, 137.5, 139.1, 158.8, 188.4.Anal. Calcd. C32H,20,: C, 87.65; H, 5.06; Found: C, 87.85; H, 5.27.

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6517 - 6531
[2]Patent: WO2014/144197,2014,A1 .Location in patent: Page/Page column 27; 28

22
2-[5-(isoqinolin-1-yl)-3-chlorophenyl]-4,6-diphenylpyrimidine [ No CAS ]
[ 100622-34-2 ]
2-[5-(anthracen-9-yl)-3-(isoquinoline-1-yl)phenyl]-4,6-diphenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; at 95℃; for 18h;Inert atmosphere;	In a stream of argon, 470 mg (1.00 mmol) of 2-[5-(isoqinolin-1-yl)-3-chlorophenyl]-4,6-diphenylpyrimidine, 289 mg (1.30 mmol) of 9-anthraceneboronic acid and 4.5 mg (20 mumol)of palladium acetate and 29.6 mg (60 mumol) of 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl were suspended in tetrahydrofuran (5.0 mL), and the suspension was heated to 95C. 900 muL (2.60 mmol) of an aqueous 3.0 M potassium carbonate solution was gradually dropwise added to the mixture, and the mixture was stirred at that temperature for 18 hours. Then the reaction mixture was left to be cooled to room temperature, and water was added to the reaction mixture. Then the deposited solid was collected by filtration to give 549 mg of target 2-[5-(anthracen-9-yl)-3-(isoquinoline-1-yl)phenyl]-4,6-diphenylpyrimidine as a white solid (yield, 90%). 1H-NMR (CDCl3) :delta.7.42 (d, J=6.5Hz, 1H), 7.44 (d, J=6.5Hz, 1H), 7.49-7.54 (m, 8H), 7.60 (t, J=7.7Hz, 1H), 7.72 (d, J=7.0Hz, 1H), 7.74 (d, J=6. 8Hz, 1H), 7.93-7.95 (m, 2H), 7.97 (d, J=8.8Hz, 2H), 8.09 (s, 1H), 8.11 (d, J=8.4Hz, 2H), 8.26-8.29 (m, 4H), 8.37 (d, J=8.5Hz, 1H), 8.59 (s, 1H), 8.73 (d, J=5. 7Hz, 1H), 8.99 (s, 1H), 9.30 (s, 1H).

Reference： [1]Patent: EP2778160,2014,A1 .Location in patent: Paragraph 0250

23
[ 100622-34-2 ]
[ 141-97-9 ]
[ 723-62-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; potassium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Inert atmosphere;	General procedure: Phenylboronic acid (0.12 g, 1.0 mmol)acetyl acetate (650mg, 5.0 mmol)CuI (19 mg, 10 mol%)K2CO3(0.28 g, 2.0 mmol) were dissolved in DMSO (5 mL, anhydrous). The solution was stirred at 100 C under nitrogen atmosphere for 24h and then cooled and the solution was poured into HCl (40 mL, 1 mol/L). The mixture was extracted with CH2Cl2 (40 mL). Then, the solution was washed with HCl (40 mL, 1 mol/l), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt 20:1) to give the desired product 3a(117 mg, 96%) as a white solid.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 5671 - 5675

24
[ 572-83-8 ]
[ 100622-34-2 ]
C₂₈H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With palladium diacetate; tetraethylammonium hydroxide; tricyclohexylphosphine; In ethanol; toluene; at 110℃;	In a 500 mL round-bottomed flask, Compound 3(0.5 g, 1.76 mmol), Compound 4 (0.58 g, 2.64 mmol),Pd(OAc)2 (11.8 mg, 0.05 mmol) and tricyclohexylphosphine(29.5 mg, 0.1 mmol) were placed with AnhydrousToluene and Ethanol. It was raised to 110 C and(Et)4NOH was added to reaction flask. After reaction iscompleted, it is extracted by Chloroform and water. Afterremoving water from the mixture, it was filtered by usingMgSO4. The mixture was columned under MC:Hexane(1:4) mixed solvent. The product was concentrated underreduced pressure and re-precipitated with methanol toobtain pure solid material. The yield was 59%.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 1850 - 1854

25
[ 100622-34-2 ]
[ 441771-49-9 ]
2',7'-di(anthracen-9-yl)spiro[cyclopentane-1,9'-[9H]fluorene] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 90℃; for 24h;Inert atmosphere;	The mixture of 2,7-dibromofluorene (3, 0.5 mmol, 1equiv), the corresponding aryl boronoic acids (1.25 mmol,2.5 equiv), 1 cm3 aqueous Na2CO3 (2.0 M), Pd(PPh3)2Cl2(0.05 mmol, 0.1 equiv) in 2 cm3 ethanol and 8 cm3 toluenewas heated to 90 C under nitrogen atmosphere for 24 h.After cooling down, the mixture was then partitioned with10 cm3 ethyl acetate and 10 cm3 water, the organic layerwas washed with saturated brine and dried over Na2SO4.After removing the solvent, the crude product was purified by column chromatography on silica gel using ethyl acetate-petroleum ether as eluent to afford the final purifiedproducts in 80-91 % yields

Reference： [1]Monatshefte fur Chemie,2015,vol. 146,p. 1519 - 1527

26
[ 64695-96-1 ]
[ 100622-34-2 ]
9-(5-fluoro-2-methyl-4-nitrophenyl)anthracene [ No CAS ]

Reference： [1]Science,2015,vol. 349,p. 1087 - 1091
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 4914 - 4918
Angew. Chem.,2016,vol. 128,p. 4998 - 5002,5

27
[ 108-86-1 ]
[ 100622-34-2 ]
[ 602-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; tetraethylammonium hydroxide; tricyclohexylphosphine In tetrahydrofuran
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 120℃; for 12h;	4; 5 Synthesis Example 4: Synthesis of Compound A13 Add 100mmol of bromobenzene, 100mmol of 9-anthracene boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water into the reaction flask, and add 1mol% of Pd(PPh3)4, and react at 120 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Among them, the added amount of Pd(PPh3)4 is 1 mol% of bromobenzene.

Reference： [1]Kang, Seokwoo; Lee, Hayoon; Kim, Beomjin; Park, Youngil; Park, Jongwook [Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 3, p. 3102 - 3105]
[2]Tu, Deshuang; Leong, Pakkin; Guo, Song; Yan, Hong; Lu, Changsheng; Zhao, Qiang [Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11370 - 11374][Angew. Chem., 2017, vol. 129, # 38, p. 11528 - 11532]
[3]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264911, 2021, A Location in patent: Paragraph 0127; 0128; 0129; 0136; 0137; 0138

28
C₅₄H₃₀Br₄ [ No CAS ]
[ 100622-34-2 ]
C₁₁₀H₆₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 70℃; for 11h;Inert atmosphere;	1. Compound [1-1] (49.72 g, 0.05 mol), 9-anthrylboric acid (49.96 g, 0.225 mol), K2CO3 (34.55 g, 0.25 mol) and 500 mL of toluene were added into a reaction kettle having a volume of 2 L under a protection of N2 atmosphere, and stirred. (0071) 2. After a temperature of the reaction kettle was increased to 70 C., a catalyst of Pd(PPh3)4 (1.16 g, 0.001 mol) and 75 mL of distilled water were added thereinto and stirred for 11 hours. After reacted sufficiently, 100 mL of distilled water was added to stop the reaction. (0072) 3. A raw product of the target product was obtained after filtered under a vacuum atmosphere, which was washed by distilled water for three times, and then recrystallized using acetone, methylbenzene and THF to obtain a solid, and obtained solid was sublimated for refinement. Lastly, after recrystallizated by methylbenzene, 52.71 g of the target compound [11] was obtained, being as a light yellow solid with a yield of 76%.

Reference： [1]Patent: US2015/376085,2015,A1 .Location in patent: Paragraph 0069-0072

29
[ 100622-34-2 ]
[ 131222-99-6 ]
6,12-di-anthracen-9-yl-chrysene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; for 5h;Inert atmosphere; Reflux;	6,12-Dibromochrysene (0.90 g, 2.33 mmol), anthracen-9-yl boronic acid (1.35 g, 6.08mmol),and Pd(PPh3)4 (0.539 g, 0.47 mmol) were added to a 100 ml/10 ml anhydrous toluene/THFsolution. Then, 2MK2CO3 solution (30ml) dissolved in H2O was added to the reaction mixtureat 50C. Themixture was refluxed for 5 h under nitrogen. After the reaction was finished,the mixture was filtered. The product was isolated using silica gel column chromatography with CHCl3 as the solvent. The solvent was removed by evaporation. Recrystallization of theresidue from CHCl3 afforded a beige compound (0.78 g, 58%). 1H-NMR (300 MHz, [D8]THF): delta = 9.07 (s, 2H), 8.99 (d, 2H), 8.75 (s, 2H), 8.21 (d, 4H), 7.63-7.55 (m, 6H), 7.52 (t,4H), 7.33-7.24 (m, 8H), EI+-Mass: 580.

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2784 - 2792
[2]Molecular Crystals and Liquid Crystals,2017,vol. 654,p. 40 - 46

30
[ 100622-34-2 ]
[ 185331-69-5 ]
9-(2-fluoro-4-nitrophenyl)anthracene [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 4995 - 4998

31
[ 19063-56-0 ]
[ 100622-34-2 ]
7-(anthracen-9-yl)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 48h;Reflux;	Intermediate 4-1 (0.300 g, 1.33 mmol), anthracen-10-yl-10-boronic acid (1.60 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.077 g, 0.07 mmol) were added to a 100 mL round-bottom flask, and a mixture of THF and 2 normal (N) K2CO3 aqueous solution (2:1 (v/v)) was added thereto, and the mixed solution was refluxed for 2 days. After completion of the reaction, water was poured into the reaction mixture, and the resulting mixture was cooled. An organic layer extracted therefrom by using CH2Cl2 (100 mL*4 times) was dried with MgSO4, and concentrated. The resulting product thus obtained was purified by silica gel chromatography while increasing the polarity of the eluent from CH2Cl2:n-hexane (at 1:2 (v/v)) to CH2Cl2:n-hexane (at 1:1 (v/v)), thereby obtaining Compound 4 (yellow powder, yield of 28%). 1H NMR (300 MHz, CDCl3) delta: 6.55 ppm (d, J=9.6 Hz, 1H), 7.35-7.41 ppm (m, 3H), 7.46-7.51 ppm (m, 3H), 7.59-7.62 ppm (m, 2H), 7.70 ppm (d, J=7.5 Hz, 1H), 7.88 ppm (d, J=9.6 Hz, 1H), 8.08 ppm (d, J=8.4 Hz, 2H), 8.56 ppm (s, 1H). 13C NMR (126 MHz, CDCl3) delta: 117.00 ppm, 118.31 ppm, 119.79 ppm, 125.43 ppm, 126.12 ppm, 126.17 ppm, 127.68 ppm, 127.93 ppm, 128.69 ppm, 129.96 ppm, 131.40 ppm, 134. 62 ppm, 143.40 ppm, 143.44 ppm, 154.29 ppm, 160.87 ppm.

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 4556 - 4567
[2]Patent: US2019/74445,2019,A1 .Location in patent: Paragraph 0215-0218

32
[ 100622-34-2 ]
[ 94-05-3 ]
[ 1210-12-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With tert.-butylhydroperoxide; copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 48h;	General procedure: To a 25 mL round flask was added the mixture of boronic acid (1) (0.3 mmol), ethyl2-cyano-3-ethoxyacrylate (2a, 0.6 mmol), CuI (0.3 mmol), t-BuOOH (0.6 mmol) in DMF (2 mL)successively. The mixture was stirred at 130 C for 24 h under air. After the reaction was completed, themixture was cooled to room temperature, diluted with water (15 mL) and then extracted withdichloromethane (5 mL × 3). The organic extract was washed with H2O (10 mL × 3) and dried overanhydrous Na2SO4. After removal of the CH2Cl2 in vacuum, the crude product thus obtained was purified bycolumn chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the desired product3
52%	With tert.-butylhydroperoxide; copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 48h;	A reaction flask was added 0.3 mmol of <strong>[100622-34-2]anthracene-9-boronic acid</strong>, 0.6 mmol of 2-cyano-3-ethoxy acrylate, 0.3 mmol of cuprous iodide, 2 ml N, N- dimethyl carboxamide, 0.3 mmol of tert-butyl hydroperoxide, in an air atmosphere, 130 C after stirring for 48 hours, heating was stopped and stirring, cooled to room temperature, evaporated under reduced pressure to give a crude product was then purified by column chromatography separation, desired product is obtained by column chromatography eluent used was a mixed solvent of petroleum ether and ethyl acetate, wherein the ratio between the volume of petroleum ether and ethyl acetate 100: 1, in 52% yield.

Reference： [1]Synlett,2016,vol. 27,p. 1979 - 1982
[2]Patent: CN104829491,2017,B .Location in patent: Paragraph 0132; 0133

33
2-[5-chloro-3-(3-pyridyl)phenyl]-4,6-diphenyl-1,3,5-triazine [ No CAS ]
[ 100622-34-2 ]
2-[5-(9-anthryl)-3-(3-pyridyl)phenyl]-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Compound C-06 2.00g (4.75mmol), 9-anthraceneboronic acid 1.37g(6.17mmol), tetrahydrofuran 30mL, palladium acetate 21.3mg (0.094mmol),2-dicyclohexylphosphino-2',4',6'-triisopropybiphenyl 90.4mg (0.19mmol) wereadded to a 100mL four neck flask, and heated at 60C under a nitrogenatmosphere for 10min. 8.55g 20%potassium carbonate aqueous solution (potassium carbonate, 1.71g (12.4mmol))was dropped into this solution, and left to react further at 70C for20hrs. Reaction mixture was cooled toroom temperature after the reaction had ended.Then, 30mL of purified water was added and it was stirred for 30min atroom temperature. The precipitated graypowder was recovered by filtering and washed sequentially with purified water,methanol, and hexane. By recrystallizingthe resulting gray powder two times from toluene, the target compound F-02 wasobtained, 1.95g (73% yield). The HPLCpurity of the target compound was 99.68%, the high-purity compound was notobtained. 0.18% symmetrical triazinecompound was detected as an impurity
65%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; at 70℃; for 17h;Inert atmosphere;	Under the flow of argon, the compound obtained in Synthesis Example 12- [5-chloro-3- (3-pyridyl) phenyl]-4,6-diphenyl-1,3,5-triazine (1.00 g, 2.38 mmol),9-anthraceneboronic acid (0.63 g, 2.85 mmol), palladium acetate (16.0 mg, 0.071 mmol),2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (67.9 mg, 0.14 mmol) was suspended in tetrahydrofuran (20 mL) and heated to 70 C. A 2M aqueous K2CO3 solution (3.56 mL, 7.13 mmol) and the mixture was stirred for 2 hours, 9-anthraceneboronic acid (0.42 g, 1.90 mmol) was added thereto,And the mixture was stirred at 70 C for 15 hours.After cooling to room temperature, water (30 mL) and methanol (30 mL) were added to the reaction mixture, and the precipitate was collected by filtration, and the precipitate obtained by filtration was sequentially washed with pure water, methanol and hexane to obtain a white powder The resulting white powder was purified by recrystallization from toluene to obtain the target product as white powder, 2- [5- (9-anthryl) -3- (3-pyridyl) phenyl] -4,6-diphenyl-1,3,5-triazine(Yield: 0.87 g, yield 65%) of the title compound (Compound A-4).

Reference： [1]Patent: JP2015/199683,2015,A .Location in patent: Paragraph 0085; 0086; 0088
[2]Patent: JP2015/34148,2015,A .Location in patent: Paragraph 0056-0057

34
[ 19821-80-8 ]
[ 100622-34-2 ]
C₂₀H₁₂Br₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 10h;Reflux;	Synthesis of compound VI Under argon, to a flask were successively added 9-anthraceneboronic acid (2.2g), 2,5-dibromoiodobenzene (3.6 g of), tetrahydrofuran (30 mL), water (30 mL), tetrakis(triphenylphosphine)palladium (100mg), potassium carbonate (2.7g), the reaction was heated at reflux for 10h. The reaction was stopped, extracted three times with ethyl acetate, the combined organic phase was then washed to neutrality; the organic phase was separated, anhydrous magnesium sulfate, filtration, spin dry; silica gel column chromatography to obtain a white solid 3.6g, yield 88%.
88%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Reflux; Inert atmosphere;	Under the protection of argon gas,is added to the flask in 9-anthracene boric acid (2.2g), 2,6-dibromine monoiodo-benzenes (3.6g), tetrahydrofuran (30 ml), water (30 ml), tetrakis(triphenylphosphine) palladium (100 mg), potassium carbonate (2.7g), heating reflux reaction 10-12 hours. Stop reaction, extraction with ethyl acetate three times, combined with the phase, then water to neutral; organic phase is separated, adds anhydrously magnesium sulfate drying, filtering, turns on lathe does ; silica gel column chromatography to obtain white solid 3.6g, yield 88%.

Reference： [1]Patent: CN105348325,2016,A .Location in patent: Paragraph 0030; 0031
[2]Patent: CN105367603,2016,A .Location in patent: Paragraph 0027 ; 0028 ; 0030

35
[ 19821-80-8 ]
[ 100622-34-2 ]
C₄₄H₃₂P₂ [ No CAS ]

Reference： [1]Patent: CN105367603,2016,A

36
(4-(10H-phenothiazine-10-yl) phenyl)(4-bromophenyl)methanone [ No CAS ]
[ 100622-34-2 ]
C₃₉H₂₅NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		The fourth intermediate (4- (10H-phenothiazine-10-yl) phenyl) (4-bromophenyl) methanone (0.50g, 1.09mmol) and 9-anthracene boronic acid (0.36g, 1.64mmol) was added to a three flask, dissolved in 30mL of tetrahydrofuran (THF), was added 2MK2CO3Aqueous solution 1.6mL, argon gas and stirred for 30min, added 0.05gPd (PPh3)4After the reaction was heated to 75 16h.After the reaction solution was cooled to room temperature, 20mL of ethanol in a rotary evaporator and spin-dry vacuum.The crude product in a volume ratio of 4: 5 mixed solution of dichloromethane and hexane as eluant purified by silica gel column chromatography, the resulting solid was dried in vacuo as a white powder, the quality 0.45g, 75% yield.

Reference： [1]Patent: CN105481794,2016,A .Location in patent: Paragraph 0072; 0073; 0074; 0075

37
[ 1073062-42-6 ]
[ 100622-34-2 ]
2-[3-chloro-5-(9-anthracenyl)phenyl]-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 70℃; for 5h;Inert atmosphere;	Under nitrogen flow,2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (30.0 g, 71.0 mmol)9-anthracene boronic acid (18.9 g, 85.2 mol),And tetrakis (triphenylphosphine) palladium (0.820 g, 0.710 mmol) were suspended in tetrahydrofuran (300 mL), and 4.0 M aqueous sodium hydroxide solution (53.2 mL, 213 mmol) was added dropwise to the obtained suspension did. The resulting mixture was stirred at 70 C. for 5 hours. After standing to cool, water (200 mL) was added, the precipitated solid was filtered off, and the solid was washed with water and methanol. The obtained solid was recrystallized (toluene) to give a pale yellow color of the desired product 2- [5- (9-anthryl) -3-chlorophenyl] -4,6-diphenyl- 1,3,5-triazine solid(Yield 32.7 g, yield 89%).
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Under the flow of argon, 2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine(14.6 g, 34.5 mmol),9-anthraceneboronic acid (10.0 g, 45.0 mmol),tetrakis(triphenylphosphine)palladium(798 mg, 0.69 mmol) ,was suspended in a toluene / ethanol (4: 1) mixture (216 mL), and then a 2.0 M aqueous solution of potassium carbonate (34.5 mL, 104 mmol) was added dropwise.Thereafter, the reaction mixture was stirred at 80 C. for 18 hours. After cooling, water was added, and the precipitated solid was separated by filtration, washed with water, methanol, and hexane, and further purified by recrystallization (toluene) to give 2- [5- (9-anthryl) -3-chlorophenyl] -4,6-diphenyl-1,3,5-triazine(Yield: 14.4 g, yield: 80%) as a yellowish white solid.
77%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 85℃; for 20h;Inert atmosphere; Reflux;	Under an argon atmosphere, 2- (3-bromo-5-chlorobenzene-1-yl) -4,6-diphenyl-1,3,5-triazine (9.78g, 23mmol), 9- anthracene boronic acid (5.13g , 23 mmol), and tetrakis (triphenylphosphine) palladium (267 mg, 0.23 mmol) was suspended in a mixed solution of toluene (780 mL) and ethanol (98 mL), and heated to 85 C.. This 1.0M- aqueous solution of potassium carbonate (69.3mL, 69.3mmol) was added dropwise slowly, and the mixture was stirred for 20 hours. After cooling, After extraction with dichloromethane, the organic layer was concentrated. The resulting crude product is recrystallized (toluene) to be a, a reaction intermediate 2- [3-chloro-5- (9-anthracenyl) phenyl] -4,6-diphenyl-1,3,5-triazine to give a white solid (yield 9.52g, 77% yield).

Reference： [1]Patent: JP2017/178931,2017,A .Location in patent: Paragraph 0069-0071
[2]Patent: JP2015/34148,2015,A .Location in patent: Paragraph 0059-0060
[3]Patent: JP2015/27986,2015,A .Location in patent: Paragraph 0351

38
[ 1057401-13-4 ]
[ 100622-34-2 ]
1,4-diketo-2,5-dioctyl-3,6-bis-(9-anthrylthiophen)pyrrolo[3,4-c]-pyrrole [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 8006 - 8013

39
4,6-diphenyl-2-[3-chloro-5-(2-pyridyl)phenyl]pyrimidine [ No CAS ]
[ 100622-34-2 ]
4,6-diphenyl-2-[5-(9-anthracenyl)-3-(2-pyridyl)phenyl]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; at 70℃; for 24h;Inert atmosphere;	Under a stream of argon, 4,6-diphenyl-2-[3-chloro-5-(2-pyridyl)phenyl]pyrimidine (840mg), 9-anthraceneboronic acid (533mg), palladium acetate (9.0mg), 2-dicyclohexylphosphino-2',4',6'--triisopropylbiphenyl (57.2 mg), 3M aqueous potassium carbonate solution (1.6 mL), were suspended in a mixed solvent of THF (10.0mL) [. After cooling the reaction mixture, water was added, followed by extraction with chloroform. The organic layer was purified by silica gel chromatography (developing solvent: chloroform) to give the desired compound 4,6-diphenyl-2-[5-(9-anthracenyl)-3-(2-pyridyl)phenyl]pyrimidine (A-4) as yellow powder (1.05g, 94% yield).; Purification Example - 4 Heating yellow powder Compound A-4 (5.00g) to 330 C under 1.0×10-3 Pa vacuum to purify by sublimation, afforded yellow powder Compound A-4 (4.00 g, 80% yield, 99% purity).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0063; 0064; 0067

40
4,6-diphenyl-2-[5-chloro-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]
[ 100622-34-2 ]
4,6-diphenyl-2-[5-(9-anthracenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; palladium diacetate; XPhos; In water; toluene; butan-1-ol; at 100℃; for 2h;Inert atmosphere;	Under a stream of argon, 4,6-diphenyl-2-[5-chloro-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine (600mg), 9-anthraceneboronic acid (403mg), palladium acetate (5.4mg), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (34.2mg), 3M potassium phosphate aqueous solution (1.2mL), were suspended in a mixed solvent of toluene (4.8mL) and 1-butanol (1.2 mL), and stirred for 2 h at 100 C. After cooling the reaction mixture, water was added, followed by extraction with chloroform. The organic layer was distilled off under reduced pressure to give target compound 4,6-diphenyl-2-[5-(9-anthracenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine (A-3) as yellow powder (584g, 76% yield).; Purification Example - 3 Heating yellow powder Compound A-3 (8.31g) to 330 C under 1.0×10-3 Pa vacuum to purify by sublimation, afforded yellow powder Compound A-3 (6.74 g, 81% yield, 99% purity or higher).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0061; 0062; 0067

41
C₃₀H₁₇ClO [ No CAS ]
[ 100622-34-2 ]
C₄₄H₂₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;	0.969 g (1.7 mmol) of Compound 2 (Yield: 81%) was synthesized as in the synthesis of Intermediate 2-1, except that 9-anthracene boronic acid and Intermediate 2-1 were used (utilized) instead of phenylboronic acid and Intermediate A, respectively.

Reference： [1]Patent: KR2015/133387,2015,A .Location in patent: Paragraph 0343; 0350-0353

42
[ 1564-64-3 ]
[ 100622-34-2 ]
[ 1055-23-8 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 13052 - 13055
Angew. Chem.,2016,p. 13052 - 13055,4

43
[ 100622-34-2 ]
[ 138505-25-6 ]
5-(anthracen-9-yl)-2-isopropoxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; water; for 22h;Reflux; Inert atmosphere;	To a solution of <strong>[138505-25-6]5-bromo-2-isopropoxybenzaldehyde</strong> (240 mg, 1.0mmol) and 2-dicyclohexylphosphino-2?, 6?-dimethoxybiphenyl (50mg, 0.13 mmol), 9-anthraceneboronic acid (244 mg, 1.1 mmol) inmixed solvent (THF : H2O = 2:1) were added K3PO4 (1.06 g, 5.0mmol), Pd(OAc)2 (10 mg, 0.05 mmol). The mixture was heated refluxtemperature under N2 in oil bath. The mixture was stirred for 22 h. The excess of K3PO4was quenched with 1 M aq. HCl. After the addition 1 M aq. HCl, extracted with ethylacetate and washed with brine. The organic layer was dried over Na2SO4, filtered andconcentrated. The residue was purified by column chromatography on silica gel (ethylacetate : hexane = 1 : 20) to give 5-(anthracen-9-yl)-2-isopropoxybenzaldehyde 6 (76.2mg, 45%) as a yellow powder. mp 140 C; 1H NMR (270 MHz, CDCl3) delta 1.53 (d, J =4.5 Hz, 6H), 4.79-4.91 (m, 1H), 7.19-7.65 (m, 8H), 7.92 (d, J = 2.7 Hz, 1H), 8.05 (d, J =8.6 Hz, 2H), 8.50 (s, 1H), 10.64 (s, 1H); 13C NMR (67.8 MHz, CDCl3)delta 22.1, 71.3, 113.9, 125.1, 125.5, 126.4, 126.9, 128.4, 130.3, 130.7, 131.0, 131.3, 135.3,138.5, 160.0, 190.0; HRMS (FAB+) m/z calcd for C24H21O2 341.1551, found 341.1543.

Reference： [1]Synlett,2016,vol. 27,p. 2352 - 2356

44
[ 100622-34-2 ]
[ 14162-95-9 ]
4-(9-anthryl)-2,2′-bipyridine [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 6327 - 6336

45
[ 150-46-9 ]
[ 1564-64-3 ]
[ 7732-18-5 ]
[ 100622-34-2 ]

Yield	Reaction Conditions	Operation in experiment
87%		As shown in Reaction Scheme 3 9-Bromoanthracene (10 g, 38.9 mmol) was added to a solution of Placed in a 3-neck round bottom flask and 300 mL of anhydrous THF under nitrogen. 2M n-BuLi (24.0 mL, 46.7 mmol) was slowly added while maintaining the temperature at -78 dege C. In the middle of the reaction, TLC was taken under the condition of EA: hexane = 1: 10, and the progress of the reaction was examined. After the spot of the reaction disappeared, triethyl borate (9.50 mL, 54.5 mmol) was added to -78 deg. The progress of the reaction was examined by taking TLC under the conditions of EA: hexane = 1: 10. After the reaction was completed, HCl (7.20 mL, 85.6 mmol) was added at room temperature, EA and H2O. A small amount of H2O in the EA layer was removed with MgSO4. After the MgSO4 was filtered off, the product in the EA layer was evaporated. The product was dissolved in a small amount of THF and reprecipitated with hexane, followed by filtration to obtain 7.55 g (yield 87%) of Compound 6 as an orange solid.
		(Synthesis of Anthracen-10-yl-10-boronic acid) 9-bromoanthracene (10 g, 38.9 mmol) was dissolved in 500 mL of anhydrous THF, and the solution was cooled down to -78 C. Then, 1.6 M n-BuLi (29.3 mL, 46.7 mmol) and triethyl borate (9.3 mL, 54.5 mmol) were added thereto, and the mixture was agitated for 30 minutes. When the reaction was complete, 2N HCl was added thereto, and the mixture was treated with ethyl acetate and water for extraction. Then, anhydrous MgSO4 was added thereto to remove moisture, a product obtained therefrom was filtered, and a solvent was removed. Hexane and ethyl acetate (50 mL) were used to perform reprecipitation. A precipitate therein was filtered, obtaining a colorless material (Intermediate (1)). 1H-NMR (300 MHz, CDCl3) delta (ppm): 8.46 (s, 1H), 8.12 (d, 2H), 8.01 (d, 2H), 7.48 (m, 4H), 5.07 (s, 2H)

Reference： [1]Patent: KR2016/39492,2016,A .Location in patent: Paragraph 0103-0107
[2]Patent: US10304637,2019,B2 .Location in patent: Page/Page column 10; 11

46
[ 3842-55-5 ]
[ 100622-34-2 ]
2-(9-anthryl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.17%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 110℃; for 12h;Inert atmosphere;	10.00 g of 9-anthraceneboronic acid (45.03 mmol) and 13.26 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (49.54 mmol) were added to a clean three-necked flask and the nitrogen was purged three times ,Then 0.26 g of tetra-triphenylphosphine palladium (0.23 mmol) was added to the flask, and nitrogen was pumped three times, and then 60 ml of a 2M potassium carbonate solution,60 ml of ethanol and 120 ml of toluene were added to the flask, and the nitrogen was pumped three times.Then stir the reaction at 110 degrees Celsius for 12 hours, stop the reaction, reduce the temperature to room temperature,The ethanol and toluene were then distilled off on a rotary evaporator. The residue was extracted three times with water and dichloromethane.The organic phase was dried over anhydrous magnesium sulfate, filtered, and then dichloromethane was distilled off.The crude product was recrystallized from toluene to obtain 17.55 g of the product. (Yield: 95.17%)
70%		Compound (3) (4.0 g, 15.0 mmol) And compound (6) (4 g, 18.0 mmol) were placed in a three-neck round bottom flask, Pd (PPh3) 4 (0.52 g, 0.45 mmol) was added under nitrogen And dissolved in 150 mL of anhydrous toluene and 16 mL of anhydrous ethanol. After stirring for 30 minutes, 2M Na2CO3 (25 mL, 45 mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours. The progress of the reaction was confirmed by TLC with MC: hexane = 1: 3 developing conditions. After the reaction was completed, the reaction mixture was extracted with chloroform and H2O. A small amount of H2O in the chloroform layer was removed with MgSO4. MgSO4 was filtered off and evaporated, followed by silica gel column chromatography under the conditions of MC: hexane = 1: 3. The obtained product was evaporated once again, and then redissolved in a small amount of THF and ethanol to obtain 4.3 g (yield 70%) of an amorphous solid compound (7).

Reference： [1]Dyes and Pigments,2018,vol. 158,p. 204 - 212
[2]Patent: CN110305114,2019,A .Location in patent: Paragraph 0038-0042; 0049-0053; 0060-0064
[3]Patent: KR2016/39492,2016,A .Location in patent: Paragraph 0103-0106; 0108

47
[ 1413732-47-4 ]
[ 100622-34-2 ]
anthracen-9-yl-trifluoromethylthioether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With oxygen; In 1-methyl-pyrrolidin-2-one; at 20℃; for 1h;	General procedure: Arylboronic acid 2 (0.12 mmol) and (bpy)Cu(SCF3) 1 (0.1 mmol) were added to a Schlenk flask fitted with magnetic stir bar and O2 balloon. The flask was evacuated and back filled with O2. The solvent NMP (2.0 mL) was added by syringe at room temperature and the solution was stirred for 1 h. For the products reported with isolated yields (3a, 3k, 3l, 3m, 3n, 3o, 3p, 3q, 3r, 3s, 3t, 3u and 3w), the reaction mixture was diluted with EtOAc, then washed with water and brine. The organic phase was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (n-hexane/ethyl acetate gradient) to afford the desired compounds. Gram-scale synthesis of compound 5 was prepared following the similar procedure. The relatively volatile products (3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j and 3v) were not isolated and their yields were determined by 19F NMR measurement in CDCl3 of the reaction mixture. For the products reported with 19F NMR yields, PhOCF3 (1.0 equiv) was added to the reaction mixture as internal standard added after the reaction completed. The reaction mixture was purified by flash chromatography on silica gel (pentane/diethyl ether gradient) to afford the desired compounds.

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 194,p. 73 - 79

48
2-(5-chloro-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
[ 100622-34-2 ]
2-[5-(9-anthryl)-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		In Example 1, 1.08 mg of palladium acetate to be used (Pd atom: 0.0048 Mmol, 0.00050-fold moles with respect to the amount used relative to the amount of compound C-1 used), 2 - dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl 4. 58 mg (0.0096 mmol), and the reaction time was changed to 13 hours, the same operation was carried out 4.90 g of the objective compound D-1 was obtained as a white powder (yield 99%). Obtained The HPLC purity of the target product was very high as 99.66%. Furthermore, once with toluene By performing recrystallization purification, the HPLC purity was 99.94%. When toluene recrystallization The recovery rate was 88%. In Example 1, 9-anthracene boronic acid was used instead of 1-naphthalene boronic acid . The same procedure was repeated except that 78 g (12.5 mmol) of the compound was used and the reaction time was changed to 10 hours to obtain 5.40 g of the objective compound D-2 as a pale yellow powder (yield 100%). The HPLC purity of the obtained product was very high as 99.54%. Further, by performing recrystallization purification once with toluene, the HPLC purity was 99.91%. Recovery rate at toluene recrystallization was 90%.

Reference： [1]Patent: JP6032000,2016,B2 .Location in patent: Paragraph 0047; 0049; 0050

49
[ 63279-58-3 ]
[ 100622-34-2 ]
C₂₄H₁₅Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	The 9 - anthracene boric acid (10mmol), 1 - bromo -4 iodine naphthalene (10mmol), potassium carbonate (30mmol), four-triphenylphosphine palladium (0.1mmol) are sequentially added to the toluene, ethanol, water in the mixed solution in the reaction temperature under the protection of nitrogen to reflux the reaction overnight. The reaction cooling to room temperature a large number of solid is separated out filtering for products obtained toluene baggy air dissolved completely after-filtration, filtrate cooling crystallization product is obtained 219 - 1 (yield 65percent).

Reference： [1]Patent: CN106565705,2017,A .Location in patent: Paragraph 0047; 0048; 0049

50
[ 25121-87-3 ]
[ 100622-34-2 ]
C₃₄H₂₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	The reaction container Riga C - 21 - 1 (2.5 g, 8.4 mmol), anthracene boric acid (3.79 g, 17 . 07 mmol), four-triphenylphosphine palladium (0.7 g, 1 . 08 mmol), potassium carbonate (5.3 g, 38.3 mmol), toluene 60 ml, ethanol 20 ml and distilled water 20 ml after 120 C is stirred under the condition 3 h. After the end of the reaction the distilled water to stop reaction, extracted with ethyl acetate. The organic layer using MgSO4Drying. For removing the solvent is distilled under reduced pressure after silica gel column purification to obtain compound 3 - 21 (3.23 g, 78%).

Reference： [1]Patent: CN107056798,2017,A .Location in patent: Paragraph 0065; 0066; 0067

51
C₃₁H₁₉BrN₂ [ No CAS ]
[ 100622-34-2 ]
C₄₅H₂₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	A reaction vessel was charged with B-15-2 (8.44 g, 16.9 mmol), anthraceneboronic acid (3.79 g, 17.07 mmol), palladium tetrakistriphenylphosphine (0.7 g, 1.08 mmol)Potassium carbonate (5.3 g, 38.3 mmol), 60 mL of toluene, 20 mL of ethanol and 20 mL of distilled water and stirred at 120 C for 3 hours.After completion of the reaction, the reaction mixture was quenched with ethyl acetate.The organic layer is dried over MgSO4.The solvent was distilled off under reduced pressure and then purified on a silica gel column to give Compound 2-15 (8.07 g, 80%).

Reference： [1]Patent: CN107311926,2017,A .Location in patent: Paragraph 0071; 0072; 0073

52
C₁₄H₇Br₂NO [ No CAS ]
[ 100622-34-2 ]
C₂₈H₁₆BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	The reaction vessel was charged with C-30-1 (6.17 g, 16.9 mmol),Dibenzofuran boronic acid (3.58 g, 17.01 mmol),Tetrakistriphenylphosphine palladium (0.7 g, 1.08 mmol),Potassium carbonate (5.3 g, 38.3 mmol),Toluene 60mL,Ethanol 20mL and distilled water 20mL,Stir at 120 C for 3h.After completion of the reaction, the reaction mixture was quenched with ethyl acetate.The organic layer is dried over MgSO4.The solvent was distilled off under reduced pressure and then purified on a silica gel column to give Compound C-30-2 (5.08 g, 65%).

Reference： [1]Patent: CN107311925,2017,A .Location in patent: Paragraph 0093; 0094; 0095

53
3,6-dibromoacridine [ No CAS ]
[ 100622-34-2 ]
C₂₇H₁₆BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	The reaction vessel was charged with 3,6-dibromoacridine (5.69, 16.9 mmol)Anthraceneboronic acid (3.79 g, 17.07 mmol),Tetrakistriphenylphosphine palladium (0.7 g, 1.08 mmol),Potassium carbonate (5.3 g, 38.3 mmol),Toluene 60mL,20mL of ethanol and 20mL of distilled water,Stir at 120 C for 3h.After completion of the reaction, the reaction mixture was quenched with ethyl acetate.The organic layer is dried over MgSO4.The solvent was distilled off under reduced pressure and then purified on a silica gel column to give Compound B-33-1 (5.87 g, 80%).

Reference： [1]Patent: CN107311925,2017,A .Location in patent: Paragraph 0070; 0071; 0072

54
C₃₁H₂₂BrN [ No CAS ]
[ 100622-34-2 ]
C₄₅H₃₁N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.29%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80 - 85℃; for 12h;Inert atmosphere;	In a 250 ml three-necked flask, under the protection of nitrogen, Intermediate 1-IV (4.88 g, 0.01 mol)9-anthraceneboronic acid(2.44 g, 0.011 mol), potassium carbonate (4.14 g, 0.03 mol),Tetrakistriphenylphosphine palladium (116 mg, 0.1 mmol), 12 mL of water and60mL of toluene, 80 ~ 85 C for 12h, after the reaction was filtered, the filtrate was evaporated under reduced pressure, purified by column chromatography, and then by toluene, The petroleum ether was recrystallized to give the desired product C01, yield 73.29%.

Reference： [1]Patent: CN107353249,2017,A .Location in patent: Paragraph 0090; 0091; 0092; 0093

55
[ 16681-56-4 ]
[ 100622-34-2 ]
C₁₇H₁₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.43 g	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 12h;	To 7.3 g (50 mmol) of <strong>[16681-56-4]<strong>[16681-56-4]2-bromo-1H-imidazol</strong>e</strong>, 11.1 g of 9-anthracene boronic acid(50 mmol) and 3.5 g (5 mmol) of bistriphenylphosphine palladium dichloride were added 130 ml of 2M aqueous sodium carbonate solution, 260 ml of methylBenzene and 86 ml of ethanol at 100 C for 12 hours. After the system had cooled down, extract with methylene chloride and wash with distilled waterThe organic phase is then washed with anhydrous magnesium sulfate and the solvent is evaporated to dryness. Column chromatography (n-hexane: dichloromethane = 20: 1)Purification gave 8.43 g of intermediate A-1.

Reference： [1]Patent: CN107383071,2017,A .Location in patent: Paragraph 0049; 0050

56
C₂₄H₂₃BrN₂ [ No CAS ]
[ 100622-34-2 ]
C₃₈H₃₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;	The reaction vessel was charged with 2-19-D (7.09 g, 16.9 mmol)Anthracene-9- boronic acid (3.75g, 16.9mmol),Tetrakistriphenylphosphine palladium (0.2 g, 0.17 mmol),Potassium carbonate (10.6 g, 76.6 mmol),Toluene 120mL, ethanol 40mL and distilled water 40mL,Stir at 120 C for 3h.After completion of the reaction, the distilled water was quenched and extracted with ethyl acetate. The organic layer is dried over MgSO4. The solvent was distilled off under reduced pressure and then purified on a silica gel column to give compound 2-19 (5.94 g, 68%).

Reference： [1]Patent: CN107382861,2017,A .Location in patent: Paragraph 0059; 0060; 0061

57
9,9'-(3'-bromo-[1,1'-biphenyl]-3,5-diyl)bis(9H-carbazole) [ No CAS ]
[ 100622-34-2 ]
9,9'-(3'-(anthracene-9-yl)[1,1'-biphenyl]-3,5-diyl)bis(9H-carbazole) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80℃; for 5h;Inert atmosphere;	3'-bromo-3,5-bis (9-carbazole) biphenyl 8.9 mmol,9-anthraceneboronic acid 9.8 mmol,0.3 mmol of tetrakistriphenylphosphine palladium and 0.02 mol of potassium carbonate were dissolved in 100 mL of toluene: H 2 O = 2: 1 mixed solvent and stirred at 80 C. for 5 h and protected by nitrogen.After TLC monitoring the reaction was completed, cooled to room temperature,After extracting with dichloromethane and water, the organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness.The product was subjected to column chromatography to obtain 9,9 '- (3' - (anthracene-9-yl) - [1,1'-biphenyl] ) 7.83 mmol, 88% yield. Mass Spectrum: 660.80.

Reference： [1]Patent: CN105968041,2016,A .Location in patent: Paragraph 0067; 0071; 0072; 0073

58
C₂₆H₁₅ClO [ No CAS ]
[ 100622-34-2 ]
C₄₀H₂₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 150℃; for 24h;	1.65 g (5 mmol) of Intermediate A, 1.81 g (15 mmol) of phenylboronic acid, 2.26 g (15 mmol) of CsF, and 1.84 g (0.25 mmol) of PdCl2(PCy3)2were dissolved in 100 ml of NMP, and the resultant solution was stirred at a temperature of 150 C. for 24 hours. After the reaction solution was cooled to room temperature, 60 ml of water was added thereto, and an extraction process was performed thereon three times by using 60 ml of ethylether. An organic layer collected therefrom was dried by using magnesium sulfate, and then, the residual obtained by evaporating a solvent therefrom was separation-purified by silica gel chromatography to obtain 1.11 g (yield: 60%) of Compound 1. 1.56 g (yield: 67%) of Compound 5 was synthesized in the same manner as in Synthesis of Compound 1, except that Intermediate 5-1 and 9-anthracene boronic acid were used instead of Intermediate A and phenylboronic acid, respectively.

Reference： [1]Patent: KR2017/128784,2017,A .Location in patent: Paragraph 0170; 0172; 0173; 0175; 0179; 0180

59
[ 100622-34-2 ]
[ 197969-58-7 ]
[ 1427213-91-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 110℃;Inert atmosphere;	In a 500 mL round-bottom flask, (4) 3.0 g (7.9 mmol),(3) 2.1 g (9.5 mmol), Pd(PPh3)4 0.37 g (0.31 mmol)were added and dissolved in anhydrous toluene 270 mLand anhydrous ethanol 30 mL, and then stirred. Whilemaintaining the nitrogen condition, the reaction temperature is raised to 110 C, and then 2 M K2CO3 20 mL(39 mmol) was added to the reaction mixture. After the reaction had finished, it was extracted with chloroform and distilled water, and the organic layer was dried withMgSO4. After column refinement of the compound withchloroform:hex= 1:10, it was reprecipitated with chloroformand methanol. (70% yield).1H-NMR (300 MHz, THF): delta (ppm) 8.56 (s, 1H), 8.09(d, 2H), 8.00 (d, 1H), 7.81 (d, 1H), 7.70 (d, 2H), 7.67 (d,1H), 7.57 (dd, 1H), 7.46 (m, 4H), 7.35 (m, 2H).

Reference： [1]Journal of Nanoscience and Nanotechnology,2018,vol. 18,p. 2166 - 2170

60
C₃₂H₁₉Br₂N [ No CAS ]
[ 100622-34-2 ]
C₄₆H₂₈BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 110℃;Inert atmosphere;	34.3 g of the intermediate k and 14.5 g of the 9-naphthalene boronic acid compound were added to a 2 L three-necked flask,Add 700ml toluene and 150ml ethanol to dissolve,Nitrogen is passed for 15 minutes and 89 ml of K2CO3 (3.0 eq., 2M) in water are added and finally added1.4g Pd(PPh3)4 (2mol%). The temperature was raised to 110C and the reaction was completed overnight. Add activated carbon adsorption, suction filtration, remove solvent, dryDry, recrystallize with toluene and ethanol to give 30.1 g of intermediate 1, yield 75%.

Reference： [1]Patent: CN107663214,2018,A .Location in patent: Paragraph 0238-0241

61
[ 100622-34-2 ]
[ 474688-73-8 ]

Reference： [1]Patent: US2018/114914,2018,A1

62
[ 5525-40-6 ]
[ 100622-34-2 ]
tetrakis(triphenylphosphine)palladium ⁽⁰⁾ [ No CAS ]
(4-(anthracen-9-yl)phenyl)diphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	1st step: (4-(anthracen-9-yl)phenyl)diphenylphosphine oxide <strong>[5525-40-6](4-bromophenyl)diphenylphosphine oxide</strong> (22.7 g, 63.5 mmol, 1.0 eq), 9-anthracene boronic acid (15.5 g, 69.9 mmol, 1.1 eq), tetrakis(triphenylphosphine) palladium(0) (1.46 g, 1.27 mmol, 2.0 mol. %) were dissolved in degassed DME (245 mL). A degassed solution of potassium carbonate (26.3 g, 190.5 mmol, 3.0 eq) in water (97 mL) was added, and the mixture was stirred 19 h at 95 C. After cooling to RT, the precipitate was filtered off and washed with DME (2*100 mL). The crude product was then dissolved in THF, and filtered over a layer of silica. The filtrate was evaporated to dryness, and the resulting solid dried in vacuum at 40 C. HPLC purity: 99.77%

Reference： [1]Patent: US2018/114914,2018,A1

63
[ 657408-07-6 ]
potassium phosphate [ No CAS ]
[ 52409-22-0 ]
(4-(10-bromoanthracen-9-yl)phenyl)diphenylphosphine oxide [ No CAS ]
[ 100622-34-2 ]
[ 96042-30-7 ]
(4-[9,9'-bianthracen-10-yl]phenyl)diphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3rd step: (4-[9,9'-bianthracen-10-yl]phenyl)diphenylphosphine oxide (4-(10-bromoanthracen-9-yl)phenyl)diphenyl phosphine oxide (5.0 g, 9.4 mmol, 1.0 eq), 9-anthracene boronic acid (3.12 g, 14.1 mmol, 1.5 eq), tris(dibenzylidenaceton)dipalladium(0) (172 mg, 0.19 mmol, 4.0 mol. %), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (308 mg, 0.75 mmol, 8.0 mol. %) and potassium phosphate (5.97 g, 28.1 mmol, 3.0 eq), were placed in a flask and suspended in toluene (20 mL). The resulting mixture was heated at 120 C. for 48 h. After cooling to RT, DCM and water were added; the organic phase was decanted and extracted with water until the aqueous was neutral. The aqueous layers were also extracted with ethyl acetate (2*200 mL) and decanted. The combined organic layers were extracted with an aqueous sodium diethylcarbamodithioate solution, decanted, dried over MgSO4, and evaporated to dryness. The crude product was then re-crystallized from 1,4-dioxane, and finally sublimed under reduced pressure. HPLC purity: 99.18% 1H NMR (CDCl3, 25 C.): delta=8.75 (s, 1H); 8.20 (d, J=8.6 Hz, 2H); 7.97 (dd, J=8.0, 11.7 Hz, 2H); 7.87 (m, 4H); 7.77 (m, 4H); 7.65 (m, 2H); 7.59 (m, 4H); 7.48 (m, 2H); 7.35 (m, 2H); 7.16 (m, 8H) ppm. 13C NMR (CDCl3, 25 C.): delta=143.62; 143.60; 137.12; 134.33; 134.05; 133.49; 133.22; 132.67; 132.56; 132.21; 131.77; 130.43; 129.27; 129.17; 127.98; 127.46; 127.41; 127.13; 126.51; 126.20; 126.14; 125.97 ppm

Reference： [1]Patent: US2018/114914,2018,A1

64
[ 2041-19-2 ]
[ 100622-34-2 ]
C₂₇H₁₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 mmol	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 3h; Inert atmosphere;	10.1 Example 10: Preparation of Compound 105 Step 1. Take 100mmol of barium borate, 100mmol of 3-bromo-9-fluorenone, 300mmol of potassium carbonate, 1mmol of tetrakistriphenylphosphine palladium, toluene, ethanol, water mixed solvent, nitrogen three times, warming to reflux for 3 hours. After completion of the reaction, the solvent was decontaminated and column chromatography yielded product 105-1 80 mmol.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN107721805, 2018, A Location in patent: Paragraph 0065; 0066; 0067

65
[ 105404-91-9 ]
[ 100622-34-2 ]
C₂₆H₁₅IS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80℃; for 12h;	Under nitrogen protection,Add to 300ml two-mouth bottle2,8-diiodo-dibenzothiophene(4.36 g, 10 mmol), 9-anthracenboronic acid (2.22 g, 10 mmol), potassium carbonate (3.45 g, 25 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), 12 mL of deionized water, and 120 mL of toluene , Heat to 80C for 12 hours. After the reaction was completed, the product was extracted with methylene chloride and washed three times with saturated aqueous sodium chloride. After the organic solvent was removed, the crude product was washed with a petroleum ether:dichloromethane=8:1 (v/v) mixed solvent. Purification by column chromatography gave 3.41 g of a nearly white solid with a yield of 70%.

Reference： [1]Patent: CN107721977,2018,A .Location in patent: Paragraph 0075; 0076; 0077; 0078; 0090

66
[ 100622-34-2 ]
C₂₄H₁₁Br₂IO [ No CAS ]
C₃₈H₂₀Br₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 110℃; for 12h;Inert atmosphere;	30.8 g (51.1 mmol) of intermediate (23) and 12.5 g (56.2 mmol) of phenylboronic acid obtained in [Reaction Scheme 28] were added.Into a 2L three-necked flask, add 600ml of toluene and 150ml of ethanol to dissolve, pass nitrogen for 15 minutes, then add 76.7mlAn aqueous solution of K2CO3 (153.3 mmol, 2 M) was added, followed by 1.2 g of Pd(PPh3)4 (2 mol%). Warming up to 110 C, reaction 12The end of the hour. Adsorption with activated carbon, suction filtration, solvent removal, drying, recrystallization from toluene and ethanol to give 23.7 g of intermediate(24), the yield was 71%.

Reference： [1]Patent: CN108148037,2018,A .Location in patent: Paragraph 0180; 0196; 0198; 0199

67
[ 100622-34-2 ]
C₁₇H₁₁F₃O₃S [ No CAS ]
[ 1370372-19-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 3h;	20 g (56.7 mmol) of compound 62-3,Anthracene-9-ylboronic acid (15.1 g, 68.1 mmol)3.2 g (2.8 mmol) of Pd (PPh3) 4 (O)And 23.5 g (170.1 mmol) of K2CO3 Toluene / EtOH / H2O mixture was added and refluxed at 80 C for 3 hours.When the reaction is complete, the mixture is extracted with EA and H2O,And dried over MgSO4. After concentration, column chromatography(column chromatography, SiO2, hexane: dichloromethane = 3: 1)To obtain Compound 62-2 (18 g, 83%).

Reference： [1]Patent: KR2018/72058,2018,A .Location in patent: Paragraph 0148; 0149; 0152; 0153

68
[ 100622-34-2 ]
[2,2'-binaphthalen]-3-yl trifluoromethanesulfonate [ No CAS ]
C₃₄H₂₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 4h;	50 g (124.2 mmol) of compound 74-3 was added to the raw wood r.b.f,Anthracene-9-ylboronic acid (33.1 g, 149.1 mmol)7.2 g (6.21 mmol) of Pd (PPh3) 4 (O)And K2CO3 (372.7 mmol) were dissolved in THF / H2O Followed by stirring at 80 C for 4 hours.After completion of the reaction, the mixture was cooled to room temperature and extracted with MCAfter washing with H 2 O, the organic layer was dried over MgSO 4.After concentration, column chromatography (SiO2, MC: hexane = 1: 10)To thereby obtain the aimed compound 74-2 (30 g, 70%).

Reference： [1]Patent: KR2018/72058,2018,A .Location in patent: Paragraph 0165; 0166; 0169; 0170

69
[ 100622-34-2 ]
C₂₄H₁₃BrO [ No CAS ]
C₃₈H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.37%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80 - 85℃; for 8h;	In a 250 ml three-necked flask, compound 1 (3.97 g, 0.01 mol), 9-indole boric acid (2.44 g, 0.011 mol), potassium carbonate (4.14 g, 0.03 mol), andTetrakistriphenylphosphine palladium (116 mg, 0.1 mmol), 12 mL water and60mL of toluene, reacted at 80-85 C for 8h, after the reaction is completed, filtered, the filtrate is desolvent under reduced pressure, purified by column chromatography, and then toluene,The petroleum ether was recrystallized to obtain the target product C02, yield: 83.37%.

Reference： [1]Patent: CN108084124,2018,A .Location in patent: Paragraph 0023

70
[ 31181-90-5 ]
[ 100622-34-2 ]
5-(anthracen-9-yl)picolinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; ethanol; water; toluene; at 50℃; for 5.5h;Inert atmosphere; Reflux;	General procedure: ((5-bromopyridin-2-yl)methylene)oxonium (0.76g, 4.08mmol), Pd(PPh3)4 (0.38g, 0.33mmol) were added to a 20ml/20ml anhydrous toluene/THF solution. Then, anhydrous ethanol 10ml and 2MK2CO3 solution (15ml) dissolved in H2O were added to the reaction mixture at 50C. Naphthalen-1-ylboronic acid (1.05g, 6.12mmol) was added after half an hour and the mixture was refluxed for 5h under nitrogen. After the reaction had finished, the mixture was filtered. The product was isolated using silica gel column chromatography with PE and EtAc (5:1) as the solvent. The solvent was removed by evaporation. Recrystallization of the residue from EtOH afforded a beige compound (0.94g, 4.03mmol, 99% yield). 2.2.3 5-(anthracen-9-yl)picolinaldehyde (4) This compound was prepared via a similar procedure for Compound 2 from ((5-bromopyridin-2-yl)methylene)oxonium (0.77?g, 4.12?mmol), and anthracen-9-ylboronic acid (1.35?g, 6.18?mmol). The product was obtained as yellow solid (0.98?g, 3.46?mmol, 62% yield). 1H NMR (400?MHz, CDCl3) delta 10.18 (s, 1H), 8.88 (s, 1H), 8.81 (s, 1H), 8.23 (s, 1H), 8.22-8.14 (m, 3H), 7.58 (d, J?=?6.0?Hz, 2H), 7.50 (d, J?=?13.2?Hz, 4H).

Reference： [1]Inorganica Chimica Acta,2019,vol. 484,p. 237 - 244

71
[ 100622-34-2 ]
C₃₀H₃₂BrNO₂ [ No CAS ]
C₄₄H₄₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 20h;	General procedure: 13-[N,N-(4-Bromophenyl)-phenyl]amino-deisopropyl dehydroabietic acid methyl ester (1.5 mmol), 9-Anthraceneboronic acid(1.0 mmol), Pd(dppf)Cl2 (0.125 mmol) dissolved in 100 mL DME, and K2CO3 (7.5 mmol) dissolved in 25 mL waterThe mixture was reacted at 90 C for 20 h after mixing. After the reaction, extraction was carried out twice with 30 mL of CHCl 3 and water, and the organic phases were combined.The solvent was removed by rotary distillation, and the crude product was purified by column chromatography, eluent: petroleum ether: ethyl acetate = 16:1. Get soilFluorescence emission spectrum of 13-[N,N-(4-mercaptophenyl)-phenyl]amino-deisopropyl dehydroabietic acid methyl ester as a yellow solid, yieldIt is 53.0%.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 12h;Inert atmosphere;	General procedure: TPA or DTPA (10 mmol), NBS (9.8 mmol), and dry acetonitrile (50 mL) were added to a flask. The mixture was stirred at room temperature in the dark for 24 h. The reaction mixture was filtered and then the obtained solid was recrystallized from methanol. Compound 1 (Br-TPA) and 2 (Br-DTPA) were obtained when TPA and DTPA, respectively, were used as starting materials. Compound 1 or 2 (5 mmol), arylboronic acid (5 mmol), and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2) (0.42 mmol) were added to a flask. An aqueous solution of K2CO3 (25 mmol, 30 mL) and DME (30 mL) were added under argon atmosphere and then the reaction mixture was heated and stirred for 12 h at 90 C. After cooling the reaction mixture to room temperature, CHCl3 (30 mL) was added and then the reaction mixture was washed with water (2 x 15 mL). The organic solvent was evaporated and the crude product was purified by column chromatography using mixtures of petroleum ether and diethyl ether (20:1 to 18:1) as the eluent. Series 1 (1a-1e) and series 2 (2a-2e) were obtained using this procedure. The synthesis and purification of series 3 (3a-3e) were the same as those used for series 1 and 2 except that the amount of NBS or arylboronic acid was doubled.

Reference： [1]Patent: CN108658801,2018,A .Location in patent: Paragraph 0032; 0039; 0040; 0045; 0046; 0048; 0050
[2]Dyes and Pigments,2020,vol. 181

72
[ 1400890-62-1 ]
[ 100622-34-2 ]
9-(3-(1,2,2-triphenylvinyl)phenyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; XPhos; In diethylene glycol dimethyl ether; water; at 90℃; for 168h;	Reagents and reaction conditions: (2-(3 -bromophenyl)ethene- 1,1 ,2-triyl)tribenzene (1 .0 eq.), anthracen-9-ylboronic acid (1.7 eq.), tetrakistriphenylphosphine palladium (0) (Pd(PPh3)4) (0.02 eq.) + [1,1 ?-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) (Pd(dppf)C12) (0.02 eq.) potassium carbonate (3.0 eq.), 2-Dicyclohexylphosphino-2?,4?,6 ?-triisopropylbiphenyl (0.05 eq.). 7 days at 90C (525mL, glyme/water 2.5/1.0).When the reaction was completed according TLC, the reaction was cooled down to room temperature. The precipitate was filtered and washed with water. Solid was dissolved in hot toluene, filtered hot over a pad of silicagel and then solvent was partially evaporated. Solid was filtered, triturated in dichloromethane (filtered hot), and recrystallized in toluene 36.1 g, (71% yield). ESI-MS: 508 (M).

Reference： [1]Patent: WO2019/72928,2019,A1 .Location in patent: Page/Page column 71
[2]Journal of the American Chemical Society,2020,vol. 142,p. 1153 - 1158

73
[ 5525-40-6 ]
[ 100622-34-2 ]
(4-(anthracen-9-yl)phenyl)diphenylphosphine oxide [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2019,vol. 7,p. 5604 - 5614

74
[ 100622-34-2 ]
C₃₁H₂₁Br [ No CAS ]
C₄₅H₃₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere;	A mixture of 3 g (6.3 mmol) of Intermediate C, 2.1 g (9.4 mmol) of anthracen-9-ylboronic acid, 0.07 g (0.06 mmol) of Pd(PPh3)4, 13 ml of 2M Na2CO3(aq), 30 ml of EtOH, and 90 ml of toluene was degassed and placed under nitrogen, and then heated at 100 C. for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature, and then filtered to give compound C15 (3.1 g, 88%). MS (m/z, FAB+): 571.5.

Reference： [1]Patent: US2019/198781,2019,A1 .Location in patent: Paragraph 0038; 0039

75
[ 100622-34-2 ]
C₁₆H₉Br₂FN₂ [ No CAS ]
C₄₄H₂₇FN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 90℃; for 12h;Inert atmosphere;	(2) Under the protection of nitrogen,6,6'-(5-fluoro-1,3-benzene)bis(3-bromopyridine) (208 mg, 0.512 mmol),9-indoleboric acid (273 mg, 1.23 mmol),Tetrakis(triphenylphosphine)palladium (29.6 mg, 0.026 mmol),Toluene (80 mL) and potassium carbonate (40 mL, 2M),The mixture was stirred in a 250 ml three-neck round bottom flask, and the mixture was heated to 90 C for 12 hours under the protection of a nitrogen gas stream.After the completion of the reaction, the mixture was cooled to room temperature. The crude product was washed with methylene chloride (40 ml) and water (4/30 mL).The crude product was purified by silica gel column chromatography using dichloromethane and n-hexane as a 1:2 solvent.It is then recrystallized from n-hexane with dichloromethane.Obtained 262mg of bright yellow crystals,Yield: 85%.

Reference： [1]Patent: CN108070004,2019,B .Location in patent: Paragraph 0097-0099; 0102-0104

76
[ 100622-34-2 ]
C₁₆H₁₀Br₂N₂ [ No CAS ]
C₄₄H₂₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 12h;Inert atmosphere;	Under the protection of nitrogen,1,3-bis[2-(5-bromopyridine)]-benzene (200 mg, 0.512 mmol),9-indoleboric acid (273 mg, 1.23 mmol),Tetrakis(triphenylphosphine)palladium (29.6 mg, 0.026 mmol),Toluene (80 mL) and aqueous potassium carbonate (40 mL, 2M),Stir in a 250 ml three-neck round bottom flask.The mixture was heated to 90 C for 12 hours under the protection of a nitrogen stream.After the completion of the reaction, the mixture was cooled to room temperature, and the crude product was washed with dichloromethane (40 ml) and deionized water (4/30 mL). The organic layer was separated, dried over magnesium sulfate, filtered and evaporated to give crude Purification by silica gel column chromatography using dichloromethane and n-hexane as a 1:2 developing solvent.It is then recrystallized from n-hexane with dichloromethane.Obtained 358mg of white crystal,The white crystal is 1,3-bis[5-(9-fluorene)-2-pyridine]-benzene.Yield: 85%.

Reference： [1]Patent: CN108070004,2019,B .Location in patent: Paragraph 0087-0089; 0091-0093

77
[ 100622-34-2 ]
[ 93-55-0 ]
[ 53744-36-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With copper(I) oxide; tert.-butylhydroperoxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In toluene; at 100℃; for 12h;Schlenk technique;	Under an atmospheric oxygen atmosphere,to a 15 mL schlenk reaction tube, phenylacetone 1c (33.5 mg, 0.25 mmol),9-anthraceneboric acid 2c (88.8mg, 0.40mmol), cuprous oxide (7.0mg, 0.05mmol),tert-butyl hydroperoxide (101.3mg, 1.125mmol),2,2,6,6-tetramethylpiperidine oxide (7.9mg, 0.05mmol) and toluene (toluene, 2.5mL) were reacted at 100 C for 12h. After the reaction was completed, the reaction mixture was cooled to room temperature and passed through celite After suction filtration, the crude product was obtained by concentration.The crude product was separated by chromatography using a prepared silica gel plate. The developing agent or eluent was petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate was 50: 1. The product (E)-3-(anthracene-9-yl)-1-phenylprop-2-en-1-one (3c). The product was a pale yellow solid with a yield of 62% (47.8 mg).

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3886 - 3892
[2]Patent: CN110194713,2019,A .Location in patent: Paragraph 0082-0088

78
[ 100622-34-2 ]
3-bromo-3',4',5'-triphenyl-1,1':2',1"-terphenyl [ No CAS ]
9-(3',4',5'-triphenyl-[1,1':2',1"-terphenyl]-3-yl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 95℃; for 22h;Inert atmosphere;	A flask was flushed with nitrogen and charged with 3-bromo-3',4',5'-triphenyl- l,l':2',l"-terphenyl (150.0 g, 1.0 eq., 279.1 mmol), anthracene boronic acid (74.4 g, 1.2 eq., 334.9 mmol), tetrakis(triphenylphosphine)palladium(0) (6.5 g, 0.02 eq., 5.6 mmol), and potassium carbonate (115.7 g, 3.0 eq., 837.2 mmol). A mixture of deaerated glyme (890 mL) and water (356 mL) was added and the reaction mixture was heated up to 95 C and left to react under nitrogen atmosphere. After 22 h of reflux, the organic layer was first decanted when hot and then cooled down while stirring. The precipitate was filtered off, rinsed first with glyme (3 x 10 mL), then with water until pH neutral (1 L) and then again with glyme (2 x 10 mL). The crude solid was dissolved in chloroform (600 mL). (0230) The resulting solution was filtered over silica using chloroform as eluent (400 mL). (0231) Hexane (100 mL) was added to the solution and the filtrate was reduced under vacuum till precipitation. Then, 200 mL of hexane were added. The suspension was stirred for 2 h at room temperature. The precipitated was filtered, rinsed with hexane and dried overnight at 40C under vacuum to afford the title compound in 74% yield (131.1 g), as a slightly yellow solid. ESI-MS: 657 (634+Na).

Reference： [1]Patent: WO2019/154713,2019,A1 .Location in patent: Page/Page column 64-65

79
[ 100622-34-2 ]
[ 84539-22-0 ]
C₂₂H₁₉N₃O [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 8825 - 8831

80
[ 124-38-9 ]
[ 100622-34-2 ]
[ 723-62-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate; In tetrahydrofuran; at 70℃; for 24h;Schlenk technique; Sealed tube;	In the glove box, add 9-anthraceneboronic acid (1mmol, 222.1mg) to a 50mL Schlenk bottle with a stir bar in order, potassium methoxide (2 mmol, 2 equivalents, 140.2 mg), Cu(IPr)Cl (0.03 mmol, 0.03 equivalents, 14.6 mg), 5 mL of solvent tetrahydrofuran. Remove the capped Schlenk bottle from the glove box, fully evacuate, fill the reaction system with carbon dioxide and seal it well, and then stir the reaction mixture at 70 C. for 24 hours. after cooling to room temperature, it was acidified by adding 1 mol / L hydrochloric acid, and extracted with ethyl acetate, and washed once with brine. The organic phase was collected and concentrated in vacuo. The liquid mixture was dropped on a silica gel column and purified by column chromatography. As petroleum ether/ethyl acetate, the desired product 9-anthracemic acid was obtained in a yield of 82%.

Reference： [1]Patent: CN110577457,2019,A .Location in patent: Paragraph 0095; 0096

81
[ 100622-34-2 ]
C₂₇H₁₇BrN₄ [ No CAS ]
C₄₁H₂₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.9%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 10h;Inert atmosphere;	After adding 10g of intermediate 4, 5.1g of compound 28-1, 5.8g of potassium carbonate, 1.35g of tetrabutylammonium bromide, 200ml of toluene, 100ml of ethanol, and 40ml of water to a 500ml three-necked bottle, the air in the system was purged with nitrogen. Add 0.12g of tetrakis (triphenylphosphine) palladium, heat to 80 and stir for 10h. After TLC detects the raw materials are completely reacted, drop to room temperature and separate the liquid. The organic phase is washed with water until neutral. Crystallization yielded a total of 10.1g of compound 28 with a yield of 83.9%

Reference： [1]Patent: CN110950846,2020,A .Location in patent: Paragraph 0097; 0101-0103

82
[ 100622-34-2 ]
[ 84-65-1 ]

Yield	Reaction Conditions	Operation in experiment
99.03%	With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 2h;	Add 0.1 mmol of 9-anthracene boronic acid, 100 ml of tetrahydrofuran and 300 ml of water to the reaction vessel, add 0.1 mmol of sodium hydroxide at the same time, and stir at room temperature for 2 hours;After the color and fluorescence of the reaction solution disappeared, it was filtered to obtain solid 9,10-anthraquinone;The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain 9,10-anthraquinone in the filtrate;The two combined, the yield of 9,10-anthraquinone was 99.03%.

Reference： [1]Patent: CN111018687,2020,A .Location in patent: Paragraph 0044-0091

83
[ 100622-34-2 ]
C₂₅H₁₃Br₂N₃ [ No CAS ]
C₃₉H₂₂BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 75 - 80℃; for 24h;Inert atmosphere;	(3) 0.08 mol of the intermediate B92 obtained aboveAdd to the reaction bottle,Continue to add raw material 0.08molD92 under the protection of nitrogen,0.00008mol tetrakis (triphenylphosphine) palladium,0.008 Tetrabutylammonium bromide,0.16mol of potassium carbonate,300mL toluene,100mL ethanol,100mL water,After stirring, the temperature was raised to 75-80 C. After 24 hours of reaction, the reaction was stopped. The reaction solution was separated after standing. The aqueous phase was extracted three times with 200 mL / times of toluene. All organic phases were combined and washed with 400 mL / times of water until neutral. The organic phase was dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure to obtain a solid crude intermediate C92. The crude intermediate C92 was recrystallized from toluene to obtain 36.75 g of pure intermediate C92 in a 75% yield.

Reference： [1]Patent: CN111100146,2020,A .Location in patent: Paragraph 0184; 0188-0189

84
[ 100622-34-2 ]
2-bromo-8,9-dimethyl-8H,9H-8,9-diaza-8a-borabenzo[fg]tetracene [ No CAS ]
C₃₄H₂₅BN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		(6) Preparation of compound NBN-An: Add 20.0 mg NBN-Br, 142.1 mg 9-anthracene boronic acid, 442.2 mg potassium carbonate, 25 ml toluene, 7 ml ethanol, and 7 ml water to the reaction eggplant-shaped bottle, and then react in the bottle The mixture was bubbled with nitrogen for 25 min; 115.0 mg of tetratriphenylphosphine palladium was added to the reaction system, and the reaction mixture was continuously bubbled for 10 min; under sealed conditions, the reaction mixture was heated to 90C while stirring with a magnet for 3 h After the reaction, the reaction solution was returned to room temperature, poured into water and extracted three times with dichloromethane, and the organic phase was collected; the solvent was removed and 201.0 mg of compound NBN-An was isolated by column chromatography, white solid, yield 80%.

Reference： [1]Patent: CN111233910,2020,A .Location in patent: Paragraph 0037

85
[ 100622-34-2 ]
[ 142137-17-5 ]
3-(9-anthryl)-5-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 80℃; for 14h;Inert atmosphere;	Into a 200 mL three-neck flask were added 1.0 g (4.3 mmol) of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong>, 2.0 g (9.2 mmol) of 9-anthraceneboronic acid, and 2.4 g (17 mmol) of potassium carbonate, and the air in the flask was replaced with nitrogen. Into the mixture were added 40 mL of tetrahydrofuran and 8 mL of water, and the mixture was degassed by being stirred under reduced pressure. Into the mixture were added 0.10 g (0.35 mmol) of tri-tert- butylphosphoniumtetrafluoroborate and 98 mg (0.11 mmol) of tris(dibenzylideneacetone)dipalladium(0), and the mixture was stirred under a nitrogen stream at 80 C for 14 hours. After the stirring, water was added to the mixture, followed by extraction of an aqueous layer with toluene. The obtained solution of the extract and an organic layer were combined and washed with water and brine, and an organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated to give a solid. The solid was purified by silica gel column chromatography (toluene: ethyl acetate = 9:1) and recrystallized with methanol to give 1.4 g of a target white solid in a yield of 98 %. Synthesis Scheme (e-1) is shown below.
98%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 80℃; for 14h;Inert atmosphere;	Add 1.0 g (4.3 mmol) of <strong>[142137-17-5]3-bromo-5-phenylpyridine</strong>, 2.0 g (9.2 mmol) of 9-anthracene boronic acid, and 2.4 g (17 mmol) of potassium carbonate to a 200 mL three-necked flask and replace the inside of the flask with nitrogen. did. 40 mL of tetrahydrofuran and 8 mL of water were added to this mixture, and the mixture was degassed by stirring under reduced pressure. To this mixture was added 0.10 g (0.35 mmol) of tri-tert-butylphosphonium tetrafluoroborate and 98 mg (0.11 mmol) of tris (dibenzylideneacetone) dipalladium (0), and under a nitrogen stream at 80 C. for 14 hours. Stirred.After stirring, water was added to the mixture and the aqueous layer was extracted with toluene. The obtained extract solution and the organic layer were combined, washed with water and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was naturally filtered and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography (toluene: ethyl acetate = 9: 1) and recrystallized from methanol to obtain 1.4 g of the desired white solid in a yield of 98%.

Reference： [1]Patent: WO2020/194097,2020,A1 .Location in patent: Paragraph 0324; 0326-0328
[2]Patent: JP2020/158497,2020,A .Location in patent: Paragraph 0324-0328

86
[ 945-51-7 ]
[ 100622-34-2 ]
[ 602-55-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With SIPr-PdCl<SUB>2</SUB>-Py; sodium t-butanolate In tetrahydrofuran at 70℃; for 12h; Inert atmosphere;

Reference： [1]Abduhulam, Hayrul; Cao, Changsheng; Chen, Qianwei; Dang, Yanfeng; Li, Chengxi; Shi, Yanhui; Wu, Shufeng; Yan, Shuqin [ACS Catalysis, 2020, vol. 10, # 15, p. 8168 - 8176]

87
[ 100622-34-2 ]
[ 100-63-0 ]
[ 602-55-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In methanol at 50℃; for 3h;	General procedure for Suzuki-Miyaura reaction General procedure: To a round bottle with a magnetic stir bar, catalyst, arylhydrazine (0.5 mmol), (hetero)arylboronic acid (0.75 mmol), Base (1.0 mmol) and 3 ml of solvent were added. The reaction mixture was conducted at 50 °C for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.

Reference： [1]Zeng, Xiao-Xiao; Li, Dong-Hui; Zhou, Zhen; Xu, Chang; Liu, Feng-Shou [Journal of Organometallic Chemistry, 2021, vol. 938]

88
[ 100622-34-2 ]
[ 19654-19-4 ]
2-(4-(anthracen-9-yl)phenyl)benzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.5%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; benzene at 78℃; for 6h; Inert atmosphere;	2.2. Synthesis of APBT, NPBT, and PPBT The chemical structures of 2-(4-(anthracen-9-yl)phenyl)benzo[d]thiazole (APBT), 2-(4-(naphth-alen-1-yl)phenyl)benzo[d]thiazole(NPBT), and 2-(4-(phenyl)phenyl)benzo[d]thiazole (or 2-(biphen-yl-4-yl)benzo[d]thiazole (PPBT) are shown in Fig. 1. The three benzothiazolederivatives were synthesized by the Suzuki-Miyaura reaction [11]. Incase of APBT, 9-anthraceneboronic acid (2.8867 g, 13 mmol), 2-(4-bromophenyl) benzothiazole (2.9018 g, 10 mmol), and Pd(PPh3)4(0.34 g, 0.3 mmol) in a mixed solvent of benzene (20 mL) and 2 M aq.Na2CO3 solution (10 mL) were added to a 100 mL three-neck roundbottomedflask under a nitrogen atmosphere. Then, ethanol (2 mL) wasadded. The solution was heated and stirred at 78 C for 6 h. After thereaction was complete, the boronic acid residue was oxidized by adding30% H2O2 and mixing for 1 h at 25 C. Then, the product was purified byrecrystallization and column chromatography. Its purity was confirmedby a single spot on the TLC, and the yield was 63.50%. APBT 1H NMR(500 MHz, CDCl3, ppm) 8.53 (s, 1H), 8.33-8.31 (d, 6H), 8.15-8.13 (d,2H), 8.08-8.06 (d, 2H), 7.98-796 (d, 4H), 7.72-7.70 (d, 4H), 7.60-7.58(d, 6H), 7.56-7.52 (t, 7H), 7.50-7.52 (m, 13H), 7.40-7.36 (t, 8H). 13CNMR (125 MHz, CDCl3, ppm) 167.83, 154.32, 141.93, 135.81, 135.20,132.96, 132.08, 131.37, 130.04, 128.46, 127.65, 127.06, 126.50,125.69, 125.22, 123.37, 121.73. FT-IR (KBr, cm 1) 3049, 2921, 1933,1603, 1478, 1454, 1433, 1400, 1357, 1313, 1244, 1222, 1190, 1108,1014. Anal Calc.(%) C:83.72, H:4.39 N:3.62 S:8.27, Found C:83.30,H:4.35 N:2.74 S:8.67. The same synthetic procedures were used for the synthesis of NPBTand PPBT. NPBT: yield (%) 72.30. 1H NMR (500 MHz, CDCl3, ppm): 8.24-8.12 (d, 2H), 8.13-8.11 (d, 2H), 7.96-7.90 (m, 6H), 7.66-7.64 (d,2H), 7.57-7.51 (m, 5H), 7.49-7.46 (t, 3H), 7.44-7.41 (t, 3H). 13C NMR(125 MHz, CDCl3, ppm): 167.79, 154.23, 143.62, 139.21, 135.11,133.83, 132.58, 131.34, 130.75, 128.40, 128.18, 127.51, 126.93,126.40, 126.33, 125.96, 125.73, 125.40, 125.25, 123.28, 121.68. FT-IR(KBr, cm 1): 3042, 1588, 1504, 1481, 1454, 1434, 1392, 1334, 1311,1248, 1226, 1186, 1117, 1017. Anal Calc.(%) C:81.90, H:4.45, N:4.15,S:9.50, Found C:83.30, H:4.35 N:2.74 S:8.67. PPBT: Yield (%) 71.50. 1HNMR (500 MHz, CDCl3, ppm): 8.18-8.17 (d, 2H), 8.10-8.06 (d, 2H),7.93-7.91 (d, 2H), 7.74-7.72 (d, 2H), 7.67-7.66 (d, 2H), 7.52-7.47 (m,5H), 7.41-7.38 (t, 3H). 13C NMR (125 MHz, CDCl3, ppm): 167.70,154.23, 143.74, 140.08, 135.07, 132.52, 128.94, 128.00, 127.96,127.66, 127.12, 126.37, 125.20, 123.22, 121.63. FT-IR (KBr, cm 1):3051, 1599, 1495, 1476, 1451, 1433, 1403, 1313, 1288, 1253, 1229,1163, 1119, 1072, 1003. Anal Calc.(%) C:79.44, H:4.53, N:4.88,S:11.14, Found C:79.05, H:3.88, N:4.45, S:12.01.

Reference： [1]Choi, Yu Bin; Kim, Dong-Eun; Lee, Burm-Jong; Lee, Jae Hyeok; Shin, Hoon-Kyu [Chemical Physics Letters, 2022, vol. 789]

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