Name: 18628-07-4|9H-3,9'-Bicarbazole|97%
Brand: Ambeed
SKU: A328047
Price: 6.0 USD
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1
[ 18628-07-4 ]
[ 108-24-7 ]
3-carbazolyl-9-acetylcarbazole [ No CAS ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

2
[ 859938-50-4 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

3
[ 56-23-5 ]
[ 86-74-8 ]
[ 31892-44-1 ]
[ 1914-12-1 ]
[ 18628-07-4 ]
[ 6515-02-2 ]
[ 83415-87-6 ]

Reference： [1]Canadian Journal of Chemistry,1982,vol. 60,p. 2442 - 2450

Yield	Reaction Conditions	Operation in experiment
84%	With dibenzo-18-crown-6; potassium acetate; copper; In N,N-dimethyl-formamide; at 120℃; for 4h;	General procedure: 2-aminobenzamide (1.4g, 0.010mol) in dibromochloromethane (2.1g, 0.010mol) dibenzo-18-crown-6 (1.1g, 0.0030mol), copper (2) (1.2g, 0.020mol), potassium acetate (2.8 g, 0.020mol), into a DMF in 100ml was reacted with stirring for 4 hours at 120 C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 1-1 1.1g (62% yield). Intermediate 1-8 (2.1g, 0.010mol) put in bromobenzene (1.6g, 0.010mol), by synthesis by the same method used in preparation Example 1-1 to give <Intermediate 1-9> 2.3g (yield 77%).
74%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;Inert atmosphere;	General procedure: 9 g (29.92 mmol) of Intermediate 1b and 50 mL of trifluoroacetic acid were dissolved in 80 mL of dichloromethane under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 30 minutes. After completion of the reaction, the reaction solution was neutralized with anhydrous MgSO4, filtered, and concentrated. The concentrated solution was recrystallized from dichloromethane and methanol, thus obtaining 6.8 g of Intermediate 1c (yield: 68%).

6
[ 867248-91-7 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With water; sodium hydroxide; In tetrahydrofuran; methanol; at 80℃; for 24h;	To a solution of 9-tosyl-9H-3,9'- bicarbazole or IC-2 (8.6 g, 17.6 mmol) in THF (150 mL) and methanol (60 mL), was added sodium hydroxide aqueous solution (10 g in 60 mL water). The mixture was heated at 80 C for 24 hours on a hot plate with a silicone oil bath. The resulting mixture was mixed with ethyl acetate and rinsed with brine, then loaded on silica gel (Grade 135) and purified by flash chromatography using eluents of ethyl acetate/hexanes (0% to 10%). After removal of solvents, the product was then collected to yield a white solid (Compound OSC-6) (5.0 g, in 86% yield). Confirmed by 1 HNMR.
77.9%	With potassium hydroxide; In tetrahydrofuran; ethanol; for 6h;Reflux;	d) 10.6 g (160.3 mmol) KOH 85% are dissolved in 450 ml EtOH, then 39.0 g (80.1 mmol) 3-Carbazol-9-yl-9-(p-tolylsulfonyl)carbazole dissolved in 180 ml THF are added and the clear solution is heated to reflux for 6 hours. The reaction mixture is cooled to RT and then added drop by drop to 1 l H2O. The resulting suspension is filtered and the residue is washed four times with H2O (200 ml each) and then dried at 80 C./125 mbar overnight to yield 25.6 g (96.1% of theory) of an off white solid. The crude product is suspended in 150 ml MeOH and heated to reflux for 2 hours. The suspension is cooled to RT and then to 0 C., filtered, washed twice with cold MeOH (20 ml each) and dried at 60 C./125 mbar overnight to yield 23.4 g (87.9%) of an off white solid. This procedure is repeated twice to yield 20.76 g (77.9% of theory) 3-Carbazol-9-yl-9H-carbazole as a white solid. 1H-NMR (400 MHz, CDCl3): delta 8.35-8.20 (m, 3H), 8.16 (br s, 1H), 8.08 (d, J=7.6 Hz, 1H), 7.64-7.28 (m, 11H).
	With sodium hydroxide; In tetrahydrofuran; methanol; water;	Step 4. 3-(9-carbazolyl)-9-tosylcarbazole (10.0 g, 21 mmol), NaOH (8.0 g, 200 mmol), 80 mL of THF, 40 mL of MeOH and 40 mL of water were added to a 500 mL round flask. The reaction was heated to reflux for 12 hours. After cooling, the mixture was purified by a silica gel column. The yield of 3-(9-carbazolyl)carbazole was 8 g.

3 g	With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;	Intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 ml) and methanol (18 ml) were added to a 100 ml three-necked round bottom flask and stirred at room temperature for 4 hours. Silica gel filtration and concentration under reduced pressure. The solid phase was washed with water and then recrystallized from dichloroethane to obtain 3 g of the title compound
3 g	With sodium hydride; In tetrahydrofuran; methanol; at 20℃; for 4h;	12 g of Intermediate 5-2, 1.0 g of sodium hydride, 36 mL of tetrahydrofuran and 18 mL of methanol were added to a 100 mL three-neck round bottom flask, and the mixture was stirred at room temperature for 4 hours. After silica gel filtration, the filtrate was concentrated under reduced pressure. The solid was washed with water and recrystallized from dichloroethane to give 3 g of the title compound.
3 g	With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;	In a 100 mL three-necked round bottom flask, intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 mL) and methanol (18 mL) were added and stirred at room temperature for 4 hours. The silica gel filter is then concentrated under reduced pressure. The solid phase was washed with water and then recrystallized with dichloroloethane to give 3 g of the title compound.

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817
[2]Patent: WO2015/195837,2015,A1 .Location in patent: Paragraph 0061; 0064
[3]Patent: US2016/248026,2016,A1 .Location in patent: Page/Page column 65
[4]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886
[5]Patent: US2009/134784,2009,A1
[6]Chemical Communications,2013,vol. 49,p. 6788 - 6790
[7]Patent: KR2017/126059,2017,A .Location in patent: Paragraph 0104; 0105; 0111; 0112
[8]Patent: KR2018/131662,2018,A .Location in patent: Paragraph 0134-0136; 0141-0142
[9]Patent: KR2019/106313,2019,A .Location in patent: Paragraph 0206-0207

7
[ 867248-84-8 ]
[ 18628-07-4 ]
[ 867248-86-0 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886

8
[ 18628-07-4 ]
[ 100-44-7 ]
9-benzyl-3-(9-carbazolyl)-9H-carbazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886

9
[ 861312-65-4 ]
[ 18628-07-4 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886
[2]Chemical Communications,2013,vol. 49,p. 6788 - 6790
[3]Patent: US2016/248026,2016,A1
[4]Patent: KR2017/126059,2017,A
[5]Patent: KR2018/131662,2018,A
[6]Patent: KR2019/106313,2019,A

10
[ 86-74-8 ]
KOH [ No CAS ]
[ 18628-07-4 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886

11
[ 52708-37-9 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

12
[ 16982-76-6 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

13
[ 859078-81-2 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

14
[ 859084-99-4 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

15
[ 86-74-8 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523
[2]Patent: US2011/309345,2011,A1
[3]Chemical Communications,2013,vol. 49,p. 6788 - 6790
[4]Patent: CN103159745,2016,B
[5]Patent: CN103694992,2016,B
[6]Patent: CN110467606,2019,A

16
[ 100-00-5 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

17
[ 88-73-3 ]
[ 18628-07-4 ]

Reference： [1]Journal of the Chemical Society,1933,p. 1523

18
[ 861312-65-4 ]
[ 18628-07-4 ]
[ 1014608-12-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817

19
[ 18628-07-4 ]
[ 15164-44-0 ]
[ 1014608-07-1 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817

20
[ 18628-07-4 ]
[ 15164-44-0 ]
[ 1009639-02-4 ]

Reference： [1]Chemical Communications,2008,vol. 8,p. 453 - 455

21
[ 109-65-9 ]
[ 18628-07-4 ]
[ 1133140-45-0 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 53 - 60

22
[ 63790-78-3 ]
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
[ 18628-07-4 ]
[ 1158807-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Step 3. The 300 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 6-chlorobenzofuro[2,3-b]pyridine (2.04 g, 10 mmol), 3-(9-carbazolyl)carbazole (3.32 g, 10 mmol), Pd(OAc)2 (450 mg, 20 mol %), P(t-Bu)3 (10 mL of 1M solution in toluene, 10 mmol), potassium tert-buthoxide (1.92 g, 20 mmol) and 150 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 36 hours. Then the reaction was cooled down to room temperature, washed with water, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 4:1, providing 3.01 g of 6-(9H-3,9'-bicarbazol-9-yl)benzofuro[2,3-b]pyridine as white solid, structure was confirmed by NMR and MS spectroscopy.

Reference： [1]Patent: US2009/134784,2009,A1

23
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
8-iodo-3,4-dihydrodibenzo[b,d]furan [ No CAS ]
[ 18628-07-4 ]
[ 1158806-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Compound 16 The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-iodo-3,4-dihydrodibenzo[b,d]furan (332 mg, 1 mmol), 3-(9-carbazolyl)carbazole (294 mg, 1 mmol), Pd(OAc)2 (23 mg, 10 mol %), P(t-Bu)3 (1 mL of 1M solution in toluene, 1 mmol), potassium tert-buthoxide (150 mg, 1.5 eq) and 100 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 410 mg of 9-(dibenzo[b,d]furan-2-yl)-9H-3,9'-bicarbazole as white solid. The structure was confirmed by NMR and MS spectroscopy.

Reference： [1]Patent: US2009/134784,2009,A1

24
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
[ 1161409-92-2 ]
[ 18628-07-4 ]
[ 1158807-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Step 3. The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-chlorobenzofuro[3,2-b]pyridine (2.04 g, 10 mmol), 3-(9-carbazolyl)carbazole (3.32 g, 10 mmol), Pd(OAc)2 (450 mg, 20 mol %), P(t-Bu)3 (10 mL of 1M solution in toluene, 10 mmol), potassium tert-buthoxide (1.92 g, 1.5 eq) and 150 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 2.5 g of 8-(9H-3,9'-bicarbazol-9-yl)benzofuro[3,2-b]pyridine as white solid. The structure was confirmed by NMR and MS spectroscopy.

Reference： [1]Patent: US2009/134784,2009,A1

25
[ 177775-86-9 ]
[ 86-74-8 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With copper oxide; KOH; In tetrahydrofuran; methanol; hexane; N,N-dimethyl acetamide; water; ethyl acetate; toluene;	Synthesis Example 4 Synthesis of Compound 2-1 A mixture of 4.0 g of 9-Acetyl-3-bromocarbazole prepared as described above and 2.8 g of carbazole were stirred together in 30 ml N,N'-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170 C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid (5.0 g) was then taken up for further deprotection using 1.2 g KOH with THF (6 ml), methanol (12 ml) and water (12 ml) at reflux temperature. The reaction mixture was then extracted using ethylacetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene:hexane (1:2) as eluent, yielded 3.8 g of 3-(9-carbazolyl)carbazole as a white powder.

Reference： [1]Patent: US2011/309345,2011,A1

26
9-benzyl-3-(9-carbazolyl)-9H-carbazole [ No CAS ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium tert-butylate; oxygen; In tetrahydrofuran; dimethyl sulfoxide; for 3h;	Into a 100 ml round bottom flask, 0.19 g of a compound C2 (0.46 mmol), 14.3 ml of DMSO, and 4.58ml of potassiumt-butoxide in THF (1 M) was added, and the mixture was stirred for 10 minutes, and then oxygen was passed for 3 hours.The mixture was poured into 200 ml of water, stirred overnight, andfiltered to give a crude product, which was purified by column chromatography to give 0.14 g of product C3 in methylene chloride: petroleum ether = 1:5 (volume ratio). 92%.
83.1%	With potassium tert-butylate; oxygen; In dimethyl sulfoxide; at 20℃; for 5h;	2) In a 250 mL three-necked flask, add 0.05 mol of intermediate F-10 and 0.5 mol of potassium tert-butoxide, add 100 mL of DMSO to dissolve it, and bubbling with oxygen at room temperature for 5 h. Observe the reaction by thin layer chromatography (TLC) until The reaction is complete. After naturally cooling to room temperature, the reaction mixture was poured into 200 mL of water and stirred for 12 h. After standing for 30 min, it was filtered. The obtained material was purified through a silica gel column to obtain intermediate II-10, with a purity of 99.65% and a yield of 83.1%.
79%	With potassium tert-butylate; oxygen; In tetrahydrofuran; dimethyl sulfoxide; for 1h;	In a 200 mL reactor, compound (10-2) (3.3 g, 7.81 mmol, 1.0 eq), potassium tert-butoxide (t-BuOK, 6.13 g, 54.6 mmol, 7.0 eq.), Dimethyl sulfoxide (DMSO, 6.1 g, 78.1 mmol, 10 eq.), Tetrahydrofuran (THF, 55 mL) was added. While this solution was stirred, oxygen bubbling was performed for 1 hour (about 10 L). To the resulting orange suspension was added city water (200 mL), neutralized with 5% aqueous ammonium chloride solution, and the organic layers extracted sequentially with toluene (100 mL) and ethyl acetate (100 mL) were combined. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give an orange brown powder (3.34 g). This was subjected to column purification (SiO2 = 80 g, hexane / chloroform = 1/1 ? 1/2) to obtain a colorless solid (2.45 g). This was dispersed and washed with ethanol and dried under high vacuum to obtain a colorless solid compound (10-3) (2.01 g, 6.23 mmol, 79%).

Reference： [1]Patent: CN108191739,2018,A .Location in patent: Paragraph 0067; 0068; 0069
[2]Chemical Communications,2012,vol. 48,p. 3015 - 3017
[3]Patent: CN110467606,2019,A .Location in patent: Paragraph 0337-0338; 0341-0343
[4]Patent: JP2019/172633,2019,A .Location in patent: Paragraph 0087; 0091; 0092

27
3-bromo-9-benzyl-9H-carbazole [ No CAS ]
[ 18628-07-4 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017
[2]Patent: CN108191739,2018,A
[3]Patent: JP2019/172633,2019,A
[4]Patent: CN110467606,2019,A

28
[ 18628-07-4 ]
[ 18737-40-1 ]
C₄₈H₃₄N₂Si [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017

29
[ 18628-07-4 ]
[ 18733-91-0 ]
9-(4-((4-bromophenyl)diphenylsilyl)phenyl)-9H-3,9'-bicarbazole [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017
[2]Chemistry - A European Journal,2014,vol. 20,p. 2149 - 2153

30
[ 18628-07-4 ]
[ 18733-91-0 ]
C₅₃H₃₇N₃Si [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017

31
[ 1401234-58-9 ]
[ 18628-07-4 ]
[ 1401234-51-2 ]

Reference： [1]Advanced Functional Materials,2012,vol. 22,p. 2830 - 2836

32
[ 1414960-14-7 ]
[ 18628-07-4 ]
[ 96042-30-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 5,5-dimethyl-1,3-cyclohexadiene;	Example 7 Synthesis of Compound 29 A suspension of (3-bromophenyl)(3-(dibenzo[b,d]furan-4-yl)phenyl)diphenylsilane (2.5 g, 4.30 mmol), 9H-3,9'-bicarbazole (1.715 g, 5.16 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol), SPhos (0.071 g, 0.172 mmol), and sodium tert-butoxide (0.826 g, 8.60 mmol) in xylene (50 mL) was refluxed at 140 C. under nitrogen overnight. After cooling to room temperature, the reaction was quenched with water and extracted with toluene. The organic phase was isolated, washed with water, and dried over MgSO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (8:2, v/v) as eluent, precipitation from DCM to ethanol to yield Compound 29 (2.86 g, 80%) as a white solid.

Reference： [1]Patent: US2012/298966,2012,A1

33
[ 1414941-45-9 ]
[ 18628-07-4 ]
[ 1414941-52-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In m-xylene; at 20℃;Inert atmosphere; Reflux;	Example 3: Synthesis of Compound 25[0114] A suspension of (3-bromophenyl)(3-(dibenzo[^

Reference： [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 59

34
[ 1414941-46-0 ]
[ 18628-07-4 ]
[ 1414941-53-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In m-xylene; at 140℃;Inert atmosphere; Reflux;	Compound 26[0117] A suspension of (3-bromophenyl)(3'-(dibenzo[^

Reference： [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 60

35
[ 1414960-14-7 ]
[ 18628-07-4 ]
[ 1414941-56-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In xylene; at 140℃;Inert atmosphere; Reflux;	Example 7: Synthesis of Compound 29[0124] A suspension of (3-bromophenyl)(3-(dibenzo[^

Reference： [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 62

36
[ 1414941-48-2 ]
[ 18628-07-4 ]
[ 1414941-60-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In m-xylene; at 140℃;Inert atmosphere; Reflux;	Example 11 : Synthesis of Compound 33 Compound 33[0137] A suspension of (3-bromophenyl)(3-(dibenzo[¾,(i]thiophen-2-yl)phenyl)diphenylsilane (3 g, 5.02 mmol), 9H-3,9*-bicarbazole (1.835 g, 5.52 mmol), Pd2(dba)3 (0.092 g, 0.100 mmol), SPhos (0.082 g, 0.201 mmol), and sodium tert-butoxide (0.965 g, 10.04 mmol) in m-xylene (50 mL) was refluxed at 140 C under nitrogen. After cooling to room temperature the reaction was quenched with water, extracted with toluene, and dried over MgSC^. Upon evaporation of the solvent, the crudue product was purified by column chromatography with hexane:DCM (8:2, v/v) as eluent to yield Compound 33 as a white powder (3.4 g, 80%). [0138]

Reference： [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 65-66

37
[ 1414941-68-6 ]
[ 18628-07-4 ]
[ 1414941-62-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In xylene; at 140℃;Reflux;	A suspension of (4-bromophenyl)(4-(dibenzo[¾,

Reference： [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 68

38
[ 16807-13-9 ]
[ 18628-07-4 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 6788 - 6790
[2]Patent: CN103694992,2016,B
[3]Patent: US2016/248026,2016,A1
[4]Patent: KR2017/126059,2017,A
[5]Patent: KR2018/131662,2018,A
[6]Patent: KR2019/106313,2019,A

39
[ 1374147-31-5 ]
[ 18628-07-4 ]
[ 1446517-60-7 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 6788 - 6790

40
(5-bromo-3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)triphenylsilane [ No CAS ]
[ 18628-07-4 ]
C₆₆H₄₄N₂SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In m-xylene; at 150℃;	A mixture of (5-bromo-3?-(dibenzo[b,d]thiophen-4-yl)-[1,1?-biphenyl]-3-yl)triphenylsilane (1.80 g, 2.67 mmol), 9H-3,9?-bicarbazole (0.89 g, 2.67 mmol), Pd2(dba)3 (0.049 g, 0.053 mmol), SPhos (0.044 g, 0.107 mmol), sodium tert-butoxide (0.77 g, 8.02 mmol) in m-xylene (100 mL) was refluxed at 150 C. overnight. After cooling to room temperature, it was passed through a short plug of Celite. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (3/1 to 2/1, v/v) as eluent to yield Compound 8 (2.2 g, 89% yield) as a white powder.

Reference： [1]Patent: US2013/293094,2013,A1 .Location in patent: Paragraph 0131

41
[ 18628-07-4 ]
[ 18733-91-0 ]
[ 1579955-07-9 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2149 - 2153

42
[ 17763-95-0 ]
[ 18628-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2596 - 2605

43
[ 1806-29-7 ]
[ 18628-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2596 - 2605

44
[ 19264-74-5 ]
[ 18628-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2596 - 2605

45
[ 858641-06-2 ]
[ 18628-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2596 - 2605

46
[ 222620-05-5 ]
[ 18628-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 2596 - 2605

47
[ 1003221-10-0 ]
[ 18628-07-4 ]
[ 1572343-36-2 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1622 - 1625

48
[ 106269-44-7 ]
[ 18628-07-4 ]
[ 1572343-37-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1622 - 1625

49
[ 3988-03-2 ]
[ 18628-07-4 ]
[ 1233215-35-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6402 - 6406

50
4-bromo-6-(triphenylene-2-yl)dibenzo[b,d]thiophene [ No CAS ]
[ 18628-07-4 ]
9-(6-(triphenylen-2-yl)dibenzo[b,d]thiophen-4-yl)-9H-3,9’-bicarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.5%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In o-xylene; for 60h;Inert atmosphere; Reflux;	9H-3,9?-bicarbazole (1.88 g, 5.66 mmol), sodium tert-butoxide (1 g, 10.42 mmol), tris(dibenzylideneacetone)palladium(0) (0.22 g, 0.240 mmol), and 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (0.5 g, 1.220 mmol) were chargedinto a reaction flask with 210 mL of o-xylenes. The mixture was degassed with nitrogen then was heated to reflux for 21/2 days. The reaction mixture was cooled to room temperature. A solid was collected via filtration. The solid wasdissolved in 1 L of hot toluene then was passed through a silica gel column. The column was flushed with hot toluene.The toluene filtrate was concentrated under vacuum. The crude solid was triturated with 300 mL of hot ethanol then wasfiltered under vacuum. The solid collected was then recrystallized twice from hot toluene to yield 9-(6-(triphenylen-2-yl)dibenzo[b,d]thiophen-4-yl)-9H-3,9?-bicarbazole (Compound 11-S) (2.25 g, 3.04 mmol, 59.5% yield) as a white solid.

Reference： [1]Patent: EP2826775,2015,A1 .Location in patent: Paragraph 0161; 0162

51
[ 1446495-82-4 ]
[ 18628-07-4 ]
C₃₈H₂₂N₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In m-xylene; for 3.5h;Inert atmosphere; Reflux;	Synthesis of Compound 7 (0160) Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonate (1.2 g, 3.09 mmol), Pd2(dba)3 (0.283 g, 0.309 mmol), dicyclohexyl(2?,4?,6?-triisopropyl-[1,1?-biphenyl]-2-yl)phosphine (0.589 g, 1.236 mmol), 9H-3-Benzo-9?-bicarbazole (1.13 g, 3.4 mmol), sodium tert-butoxide (0.475 g, 4.94 mmol) and 50 mL of m-xylene were charged in a 100 mL flask. The mixture was bubbled with N2 for 30 minutes then heated to reflux for 3.5 hours. The reaction was cooled down and subjected to aqueous workup. After workup, 1.2 g (68%) white solid product was obtained which was confirmed by NMR.

Reference： [1]Patent: US8969592,2015,B2 .Location in patent: Page/Page column 121; 122

52
[ 36822-09-0 ]
[ 18628-07-4 ]
C₃₄H₂₀N₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 18h;Reflux;	4-Chlorobenzo[4,5]thieno[3,2-d]pyrimidine (1.992 g, 9.03 mmol) and 9H-3,9'-bicarbazole (2.000 g, 6.02 mmol), sodium 2-methylpropan-2-olate (1.156 g, 12.03 mmol), Pd2(dba)3 (250 mg) and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhOS) (310 mg) were suspended in xylene (100 ml), degassed and heated to reflux for 18 hr. The reaction solution was cooled down, filtered through celite plug and evaporated. Column chromatography on silica gel column, eluted with hexane/DCM 1/1 (v/v), then hexane/EtOAc 4/1 (v/v), followed by crystallyzation from hexane/DCM provided yellow crystals (2.8 g, 90% yield).

Reference： [1]Patent: EP2910555,2015,A1 .Location in patent: Paragraph 0077-0078

53
[ 3740-92-9 ]
[ 18628-07-4 ]
C₅₈H₃₆N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.4%		3.00 g of 3,9?-bi-9H-carbazole (9.03 mmol) was placed ina 300-mE three-neck flask, the interior of the flask was sub-stituted with nitrogen, and 50 mE of tetrahydrofuran was added thereto. The solution was stirred at ?78° C. for 20 minutes. 6.77 mE of a 1.60 mol/E hexane solution of n-butyllithium (10.8 mmol) was added dropwise to the solution with a syringe. The solution was stirred under a nitrogen atmosphere at ?78° C. for 2 hours.After stirring, a mixed solution of 0.924 g of 4,6-dichioro- 2-phenylpyrimidine (4.11 mmol) and 20 mE of tetrahydroth10 ran was added to the solution, followed by stirring. The solution was slowly returned from ?78° C. to room temperature,and then the solution was stirred at 80° C. for 10 hours.After stirring, 100 mE of water was added to the solution,followed by stirring. After stirring, toluene was added to themixture, which was thus extracted therewith. Afier extracting, the organic layer and the aqueous layer were separated, and the organic layer was dried with magnesium sulfateadded thereto. After drying, the mixture was filtered to pro-vide a filtrate.The resulting filtrate was concentrated and purified by silica gel column chromatography. After puri1zing, the purified product was thrther purified by GPC to provide a solidmattet The resulting solid matter was recrystallized from a mixed solvent of chloroform and methanol, thereby providing a compound 4 in the form of white powder solid with a yield amount of 0.651 g (yield: 19.4percent). The identification of the compound was performed by ?H-NMR, ?3C-NMR and elemental analysis.?H-NMR (500 MHz, CDC13, TMS, oe): 8.78-8.76 (m, 2H), 8.54 (d, J=9.OHz, 2H), 8.31 (d, J=2.OHz, 2H), 8.26 (d, J=8.5Hz, 2H), 8.19 (d, J=8.OHz, 4H), 8.13 (d, J=7.5 Hz, 2H), 7.98 (s, 1H), 7.72 (dd, J=9.0 Hz, 2.0 Hz, 2H), 7.66-7.59 (m, 5H),7.46-7.41 (m, 1OH), 7.33-7.31 (m, 4H)?3C-NMR (125 MHz, CDC13, oe): 165.95, 160.41, 141.61,139.43, 138.00, 136.89, 132.29, 131.91, 129.05, 128.67,127.53, 126.69, 126.20, 126.00, 125.06, 123.31, 122.77,120.87, 120.38, 119.89, 119.37, 114.05, 112.60, 109.74,103.48Elemental analysis: calculated for C58H35N5: C, 85.27percent;H, 4.44percent; N, 10.29percent. found: C, 84.97percent; H, 4.36percent; N,10.40percent

Reference： [1]Patent: US9153788,2015,B2 .Location in patent: Page/Page column 99; 100

54
[ 1193-21-1 ]
[ 18628-07-4 ]
C₅₂H₃₂N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29.7%		4.00 g of 3,9?-bi-9H-carbazole (12.0 mmol) was placed in a 300-mE three-neck flask, the interior of the flask was substituted with nitrogen, and 100 mE of tetrahydroffiran wasthen added thereto, followed by stirring at -78 C. for 20 minutes. 9.03 mE of a 1.60 mol/E hexane solution of n-butyllithium (14.4 mmol) was added dropwise to the solution with a syringe.The solution was stirred under a nitrogen atmosphere at-78 C. for 2 hours. Afier stirring, a mixed solution of 0.813 g of 4,6-dichioropyrimidine (5.45 mmol) and 20 mE of tetrahydrofuran was added to the solution, followed by stirring. The solution was slowly returned from -78 C. to room temperature, and then the solution was stirred at 80 C. for 5 hours.Afier stirring, 100 mE of water was added to the solution, followed by stirring. After stirring, toluene was added to the mixture, which was thus extracted therewith. Afier extracting, the organic layer and the aqueous layer were separated,and the organic layer was dried with magnesium sulfate added thereto. Afier drying, the mixture was filtered to provide a filtrate.The resulting filtrate was concentrated and purified by silica gel column chromatography. After puri1zing, the purified product was thrther purified with a GPC preparative colunm to provide a solid mattet The resulting solid matter was added to a mixed solvent of toluene and methanol, followed by heating to 60 C. Afier heating, the mixture was suction-filtered to recover a solid matter, thereby providing a compound 40 in the form of white powder solid with a yield amount of 1.20 g (yield: 29.7%). The identification of the compound was performed by ?H-NMR, ?3C-NMR and elemental analysis.?H-NMR (500 MHz, CDC13, TMS, oe): 9.45 (s, 1H), 8.50 (d, J=8.5 Hz, 2H), 8.29 (d, J=1.5 Hz, 2H), 8.21-8.18 (m, 6H), 8.13-8.11 (m, 3H), 7.70 (dd, J=8.5 Hz, 2.0 Hz, 2H), 7.59 (t, J=7.7 Hz, 2H), 7.46-7.41 (m, 1OH), 7.34-7.30 (m, 4H)?3C-NMR (125 MHz, CDC13, oe): 160.12, 159.96, 141.55,139.24, 137.84, 132.49, 127.58, 126.79, 126.24, 126.00,125.16, 123.31, 122.98, 120.91, 120.39, 119.91, 119.33,114.17, 112.46, 109.70, 105.57Elemental analysis: calculated for C52H32N5: C, 84.30%; H, 4.35%; N, 11.34%. found: C, 84.17%; H, 4.27%; N, 11.33%

Reference： [1]Patent: US9153788,2015,B2 .Location in patent: Page/Page column 100; 101

55
[ 108-77-0 ]
[ 18628-07-4 ]
9,9'-(6-chloro-1,3,5-triazin-2,4-diyl)-bis-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.67 g		3,9?-bi-9H-carbazole (2.71 g, 8.15 mmol) was placed in a three-neck flask, the interior of the flask was substituted with nitrogen, and 50 mE of tetrahydrofuran was added thereto, followed by stirring for 10 minutes. After stirring, the solution was cooled to -78 C. and stirred for 20 minutes. After stirring, a 1.60 M hexane solution of n-butyllithium (5.00 mE, 8.00 mmol) was added thereto with a syringe, and the solution was stirred at -78 C. for 2 hours. The solution was then added to a mixture of 2,4,6-trichloro-1,3,5-triazine (0.740 g, 4.01 mmol) and 20 mE oftetrahydrofuran through a droppingfunnel. The mixture was stirred at 70 C. for 8 hours, and then water was added thereto, followed by further stirring for 30 minutes. Thereafter, chloroform was added to the mixture, which was thus extracted therewith. After separating the organic layer and the aqueous layer, the organic layer wasdried with sodium sulfate added thereto, and was suction- filtered to provide a filtrate. The resulting filtrate was purified by column chromatography, thereby providing 9,9?-(6-chloro-1 ,3,5-triazin-2,4-diyl)-bis-9H-carbazole with a yield amount of 2.67 g (yield: 85.80).

Reference： [1]Patent: US9153788,2015,B2 .Location in patent: Page/Page column 97; 98; 99

56
[ 1592-95-6 ]
[ 86-74-8 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
79.6%	With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; for 12h;Reflux;	After introducing 9H-carbazole (20 g, 119.6 mmol), 3-bromo-9H-carbazole (35.3 g, 143.5 mmol), copper(I) iodide (59.8 g, 59.8 mmol), cesium carbonate (97.4 g, 229 mmol), ethylene diamine (7.18 g, 119.6 mmol), and toluene(600 mL) into a flask, the mixture was stirred under reflux for 12 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate, washed with purified water, dried with anhydrous MgSO4, and distilled under reduced pressure. The residues were purified by column chromatography to obtain compound 2-1 (31.6 g, yield: 79.6%)
79.6%	With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; at 20℃; for 12h;	9H-carbazole (20 g, 119.6 mmol),3-Bromo-9H-carbazole(35.3 g, 143.5 mmol),Copper (I) Iodide(59.8 g, 59.8 mmol),Cesium carbonate (97.4 g, 229 mmol),Ethylenediamine (7.18 g, 119.6 mmol) And 600 mL of toluene, and the mixture was stirred under reflux for 12 hours.Cooled to room temperature, extracted with ethyl acetate, and washed with purified water. Dried over anhydrous magnesium sulfate, and distilled under reduced pressure. The resulting residue was subjected to column chromatography to obtain Compound 2-1 (31.6 g, yield 79.6%).

Reference： [1]Patent: WO2015/167300,2015,A1 .Location in patent: Paragraph 171; 172; 173
[2]Patent: KR2016/11463,2016,A .Location in patent: Paragraph 0052-0054

57
[ 18628-07-4 ]
C₃₂H₁₈N₄ [ No CAS ]

Reference： [1]Patent: WO2015/167300,2015,A1
[2]Patent: KR2016/11463,2016,A

58
[ 2213-63-0 ]
[ 18628-07-4 ]
C₃₂H₁₉ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 1h;	After introducing compound 2-1 (15.1 g, 45.4 mmol), sodium hydride (60%) (2.2 g, 54.5 mmol), 1,2-dichloroquinoxaline (10.8 g, 54.5 mmol), and DMF (200 mL) into a flask, the mixture was stirred at room temperature for 1 hour. Methanol and purified water were added to the mixture to obtain a solid substance. The solid substance was filtered, and dried under reduced pressure to obtain compound 2-2 (21 g, 94 %).
94%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 1h;	Compound 2-1(15.1 g, 45.4 mmol),NaH (60% in mineral oil)(2.2 g, 54.5 mmol),2,3-Dichloroquinoxaline (10.8 g, 54.5 mmol)And 200 mL of DMF were added, and the mixture was stirred at room temperature for 1 hour.Methanol and purified water were added to produce a solid. The solid was filtered and dried under reduced pressure to obtain Compound 2-2 (21 g, yield: 94%).

Reference： [1]Patent: WO2015/167300,2015,A1 .Location in patent: Paragraph 171; 174; 175
[2]Patent: KR2016/11463,2016,A .Location in patent: Paragraph 0052; 0055-0056

59
5-iodoindolo[3,2,1-jk]carbazole [ No CAS ]
[ 18628-07-4 ]
C₄₂H₂₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In m-xylene; for 16h;Reflux;	9H-3,9?-bicarbazole (4.2 g, 12.7 mmol), 5-iodoindolo[3,2,1-jk]carbazole (3.9 g,10.6 mmol), Pd2(dba)3 (0.20 g, 0.21 mmol), dicyclohexyl(2?,6?-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine (0.35 g, 0.85mmol) and sodium tert-butoxide (3.1 g, 31.9 mmol) were added to m-xylene (100 mL) and the mixture thoroughlydegassed before being heated to reflux for 16 hours. The crude reaction mixture was cooled and filtered through celiteand washed with DCM and hot toluene. The filtrate was reduced and the crude material was chromatographed on silicagel with 9/1 heptane/DCM to 7/3 heptane/DCM to give 5.5 g (91 %) of a Compound 13 as white solid.

Reference： [1]Patent: EP2927234,2015,A1 .Location in patent: Paragraph 0100

60
[ 1592-95-6 ]
[ 18628-07-4 ]

Reference： [1]Patent: WO2015/195837,2015,A1
[2]Patent: CN103159745,2016,B
[3]Patent: KR2016/113487,2016,A
[4]Patent: CN108191739,2018,A
[5]Patent: JP2019/172633,2019,A

61
[ 177775-88-1 ]
[ 18628-07-4 ]

Reference： [1]Patent: WO2015/195837,2015,A1

62
[ 18628-07-4 ]
C₂₁H₁₂BrNS [ No CAS ]
C₄₅H₂₇N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 5h;	Compound 10-3 5g (12.81mmol ) and 9H-3,9'-bicarbazole 5.1g(15.37mmol),Pd(PPh3)4 0.74g (0.64mmol), K2CO3 3.5g (25.62mmol) toluene 50ml,ethanol (EtOH) 5ml and 5ml H2O was refluxed at 120C for 5 hour.After cooling to room temperature after completion of the reaction and extracted with distilled water and EA (ethyl acetate). The organic layer was dried over anhydrous MgSO4 then the solvent removed by rotary evaporator and EA (ethyl acetate) and hexane (Hexane) gave after washing to give 6.3g the title compound 156 (77%).

Reference： [1]Patent: KR2016/1702,2016,A .Location in patent: Paragraph 0289-0290; 0297-0298

63
[ 78941-29-4 ]
[ 18628-07-4 ]
9-[bis(3-methylphenyl)-1,3,5-triazin-2-yl]-3-(9H-carbazol-9-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		The synthetic example 4 preparation - (9-carbazolyl) carbazole (3.8g) dryunder nitrogen dissolved in 60mL, N N, -dimethylformamide Join0.7G Sodium hydride and stirring at roomtemperature for 1 hours. then willdissolve Drying N, N '- dimethylformamide , 2-chlorol-46-di (3- methyl phenyl) -1, 3, 5-triazine (U-2, 4.0g) Solution (25mL) wasadded to the reaction mixture. To further stir 3 hours Reaction mixture into the water, productprecipitated,With the use of methanol use Hexanecleaning Geta solid and under vacuum dryingIn order to obtain, 5.8G 2, 4- di(3- methyl phenyl) -6- (3-N- carbazolylcarbazole) -9 '- YL) -1, 3, 5- in triazine, 2-11(89)Compound2-11 (89%)

Reference： [1]Patent: CN103159745,2016,B .Location in patent: Paragraph 0124-0125; 0216; 0218-0221

64
[ 3842-55-5 ]
[ 18628-07-4 ]
[ 1352749-89-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		3-(9-carbazolyl) carbazole (3.8g) under nitrogen dissolved in 60 ml dry N, N '-dimethyl formamide. Adding 0.7g of sodium hydride, and stirring at room temperature 1 hour. N then dissolved in dry, N '-dimethyl formamide in the 2-chloro -4, 6 diphenyl -1, 3, 5-triazine (U-1, 3.6g) solution (25 ml) is added to the reaction mixture. The reaction further stirring 3 hours. In water is poured into the reaction mixture, to precipitate the product. Then with methanol-hexane for cleaning solid, and drying under vacuum, in order to obtain 5.4g of the 2, 4-diphenyl-6-(-carbazolyl 3-N) carbazole -9 the [...] -yl)-1, 3, 5-triazine, i.e. compound 2-1 (84%).

Reference： [1]Patent: CN103159745,2016,B .Location in patent: Paragraph 0124-0125; 0205; 0207-0209
[2]Chemical Communications,2016,vol. 52,p. 10032 - 10035

65
3-carbazolyl-9-acetylcarbazole [ No CAS ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide;Reflux;	Carbazolyl-9-acetylcarbazole (1.38 g, 3.7 mmol), KOH (2.0 g, 35. 7 mmol), 10 mLTHF, 5 mL DMSO and 2 mL water were placed in a 100 mL round bottom flask. The reaction was heated to reflux for 4 h and the reaction was monitored by TLC.After the reaction is completed, the THF is poured out and poured into the water to precipitate, and the crude product obtained by suction filtration and drying is recrystallized with EtOH,The amount of activated carbon decolorization, and ultimately get the white crystal 97g; yield of 95%.
3.8 g	With potassium hydroxide; In tetrahydrofuran; methanol; water;	for further deprotection reaction, the de-protection reaction is used under the temperature in the backflow 1.2g THF potassium hydroxide (KOH) and tetrahydrofuran (6 ml), methanol (12 ml) and water (12 ml) to. Then use the ethyl acetate extraction reaction mixture; in anhydrous sodium sulfate and organic layer is dried, and is evaporated under the vacuum to dry. Then use toluene: hexane (the 1 [...] 2) as a least silicon oxide gel column chromatography of the white powder of outputs 3.8g the 3-(9-carbazolyl) carbazole.

Reference： [1]Patent: CN103694992,2016,B .Location in patent: Paragraph 0104-0107
[2]Patent: CN103159745,2016,B .Location in patent: Paragraph 0125; 0206

66
[ 177775-86-9 ]
[ 18628-07-4 ]

Reference： [1]Patent: CN103159745,2016,B

67
[ 18628-07-4 ]
C₂₁H₁₅ClO₂ [ No CAS ]
C₄₅H₃₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 5h;Inert atmosphere; Reflux;	Preparation Example 1 obtained in Inv 1 (2.8g, 8.5 mmol), 9H3,9'noncarbazole(3.4 g, 10.2 mmol) in toluene (85 ) andthen dissolved in, Pd2 (dba) 3 (0.76g , 0.8mmol) was added under nitrogen. Thereafter, this was placed in the NaOtBu (2.4g,25mmol), (tBu)3P were introduced into a (0.8 , 0.8mmol) to the reaction solution, the mixture was stirred under reflux for 5hours. After confirming that the reaction was completed by TLC, it cooled to room temperature. After the reaction, distilled water theorganic layer was extracted with ethyl acetate. The resulting organic layer was dried with Na2SO4 and evaporated underreduced pressure, and then purified by column chromatography to give the compound Cpd 6 (4.8g, 80% yield).

Reference： [1]Patent: KR2016/76367,2016,A .Location in patent: Paragraph 0379-0382

68
[ 18628-07-4 ]
[ 118527-30-3 ]
9-(2,6-bis(trifluoromethyl)phenyl)-9H-[3,9′]bicarbazolyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; In para-xylene; for 16.0h;Reflux;	General procedure: 12.6 g (38.32 mmol) of 9H-[3,9?]bicarbazolyl [18628-07-4], 7 g (38.32 mmol) of 2-bromo-1,3-ditrifluoromethylbenzene [118527-30-3] and 16 g of K2CO3are suspended in 300 mL of p-xylene. To the suspension are added 0.86 g (3.84 mmol) of Pd(OAc)2and 7.6 mL of a 1M tri-tert-butylphosphine solution. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, washed three times with 200 mL of water and then concentrated to dryness. The residue is subjected to hot extraction with toluene, recrystallized from toluene and finally sublimed under high vacuum. Yield: 14.5 g (35 mmol), 87% of theory; purity 99.9%

Reference： [1]Patent: KR2015/132872,2015,A .Location in patent: Paragraph 0249-0251

69
[ 383-29-9 ]
[ 18628-07-4 ]
4,4'-bis(3-carbazolyl)carbazolediphenyl sulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium tert-butylate; In N,N-dimethyl-formamide; at 110℃; for 12h;	A solution of intermediate 3, 6-dicarbazolylcarbazole (1.4 g, 0.0028 mol) was dissolved in 20 mL of DMF (dimethylformamide), and potassium tert-butoxide (0.32 g, 0.003 mol (0.33 g, 0.0013 mol) was added and the temperature was increased to 110 C for 12 h. The reaction was stopped and the reaction mixture was cooled and poured into 200 mL of water. The reaction mixture was heated at 60 C for 30 min, Precipitate, filter, washed with water several times; the solid dissolved in 100mL dichloromethane into a solution, adding an appropriate amount of anhydrous sodium sulfate drying, filtration; filtrate by adding 200mL acetone, the use of rotary evaporator distillation of dichloromethane and large Part of the acetone to be precipitated, filtered, washed with a small amount of acetone 3 times, vacuum drying white powder 1. 25g, 80% yield.

Reference： [1]Patent: CN103694992,2016,B .Location in patent: Paragraph 0091; 0108-0111

70
[ 861622-97-1 ]
[ 18628-07-4 ]

Reference： [1]Patent: CN103694992,2016,B

71
[ 1442648-14-7 ]
[ 18628-07-4 ]
8-(3-carbazol-9-ylcarbazol-9-yl)dibenzofuran-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.9%	With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline; In 1,3,5-trimethyl-benzene; for 48h;Reflux;	e) 7.78 g (23.4 mmol) 3-Carbazol-9-yl-9H-carbazole, 5.50 g (19.5 mmol) 8-Bromodibenzofuran-2-carbonitrile,1.11 g (5.8 mmol) Cul, 2.32 g (11.7 mmol) 1,10-Phenanthroline and 13.3 g (62.4 mmol) K3PO4 are suspended in 200 ml Mesitylene and heated to reflux for 48 hours. The resulting suspension is diluted with 50 ml Toluene, filtered hot through Hiflo and the residue is washed three times with Toluene (50 ml each). To the filtrate are added 30 g Silica, the suspension is heated to reflux for 1 hour, filtered hot and the residue is washed three times with Toluene (50 ml each). The filtrate is cooled to RT, dried with MgSO4, filtered and evaporated to yield 14.1 g (138.7% of theory) of a slightly brown solid. To the crude product 100 ml MeOH are added and the suspension is heated to reflux for 1 hour, then cooled to 0 C., filtered, washed three times with MeOH (20 ml each) and dried at 60 C./125 mbar overnight to yield 10.1 g (98.9% of theory) of a beige solid that is further purified by chromatography (solvent gradient: Heptane/CH2Cl2) to yield 5.81 g (56.9% of theory) 8-(3-carbazol-9-ylcarbazol-9-yl)dibenzofuran-2-carbonitrile as a white solid. 1H-NMR (400 MHz, CDCl3): delta 8.33 (d, J=1.6 Hz, 2H), 8.26 (d, J=2.0 Hz, 1H), 8.20 (d, J=8.0 Hz, 2H), 8.16 (d, J=7.6 Hz, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.83 (txd, J1=8.8 Hz, J2=1.6 Hz, 2H), 7.77 (d, J=8.8 Hz, 1H), 7.59-7.29 (m, 11H).

Reference： [1]Patent: US2016/248026,2016,A1 .Location in patent: Paragraph 0150; 0151

72
[ 177775-88-1 ]
[ 86-74-8 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
43 g		Substituent 3a (75 g) and carbazole (34 g) were dissolved in DMF (1 L) in a 2 L 3-neck round bottom flask. After 1 hour, potassium carbonate (77 g), copper powder (35 g) and copper iodide (17 g) were added, and the mixture was stirred under reflux. After 12 hours, the reaction mixture was cooled to room temperature, and potassium hydroxide was added thereto, followed by stirring for 1 hour. The reaction mixture was layered with water and ethyl acetate to remove water, and the organic layer was washed twice with water.The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent. The material produced by concentration was subjected to column separation to obtain 43 g of the title compound.

Reference： [1]Patent: KR2016/113487,2016,A .Location in patent: Paragraph 0070; 0076; 0077

73
[ 1352226-51-7 ]
[ 18628-07-4 ]
C₃₇H₂₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5 g	With copper; potassium hydroxide; In N,N-dimethyl-formamide;Heating;	intermediate 2-1 (5 g), 3,9 '-bicarbazole (9 g), copper powder (2.3 g) and potassium hydroxide (2 g) were dissolved in DMF (100 ml) and stirred with heating in a 250 ml three-necked round bottom flask .The reaction solution was layered to remove water, and the organic layer was washed twice with water.The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent.The material formed by concentration was dissolved in ethyl acetate and hexane5 g of the title compound 2 was obtained through separation of the used column.

Reference： [1]Patent: KR2016/113487,2016,A .Location in patent: Paragraph 0070; 0071; 0078; 0079

74
[ 18628-07-4 ]
C₃₁H₂₄BrN₃ [ No CAS ]
C₅₅H₃₉N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos; In 1,4-dioxane; at 110℃; for 24h;Inert atmosphere;	In a 20-mL glass tube equipped with a screw cap, was placed p-CP-Br/Trz (0.259 g), 9H-3,9?-bicarbazole (0.133 g), NaOtBu (0.063 g), Pd2(dba)3 (0.092 g) and tBuXPhos (0.13 3 g). The tube was evacuated/refilled with argon three times and then added 1,4-dioxane (2.5 mL) under argon. The mixture was stirred at 110 C for 1 d. For work-up, the mixture was diluted with DCM and filtered through silica gel. The volatiles were removed under vacuum, and flash chromatography (gradient 0-30% dichloromethane in hexanes) was used to purify the product. The curde product obtained from chromatography was furthure purified by trituration with methanol. Yield: 0.080 g, 26%.Photoluminescent characterization of p-CP-(N-CzCz)/Trz: maximum emission wavelength: 438 nm (in toluene, r.t.), 514 nm (in dichloromethane, r.t.), 456 nm (thin film);Photoluminescent quantum yields (PLQY): 0.08 (under air, in toluene), 0.20 (under N2, in toluene).

Reference： [1]Patent: WO2016/196885,2016,A1 .Location in patent: Page/Page column 57; 58

75
[ 134450-56-9 ]
[ 18628-07-4 ]
4,5-di(9H-[3,9'-bicarbazol]-9-yl)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		Sodium hydride (60% in oil, 0.16 g, 3.98 mmol) and 9H-3,9'-bicarbazole (0.85 g, 2.53 mmol) were stirred in 3 ml anhydrousDMF solvent under a nitrogen atmosphere. After 20 min, 4,5-difluorophthalonitrile (0.20 g, 1.21 mmol) in 5 ml DMF was addedthe mixture. The reaction mixture was stirred at room temperaturefor 1 h. The reaction mixture was quenched with distilled water.Organic layer of the mixture was extracted with dichloromethaneand distilled water. Then solvent of organic layer was evaporatedand purified by column chromatography (dichloromethane/nhexane).The yellow product final purified by sublimation. The lightyellow product was obtained in 50% yield (0.48 g).1H NMR (500 MHz, CDCl3): delta 8.36 (d, J = 2.5 Hz, 1H), 8.19-8.16(m, 1H), 8.16-8.09 (m, 5H), 7.94 (d, J = 3.5 Hz, 1H), 7.87 (d,J = 3.7 Hz, 3H), 7.80 (d, J = 2.5 Hz, 1H), 7.51 (d, J = 4.2 Hz, 1H),7.42-7.40 (m, 1H), 7.29-7.09 (m, 15H), 6.80-6.78 (m, 3H). 13C NMR(125 MHz, CDCl3): delta 141.65, 141.40, 140.06, 140.01, 139.81, 139.65,138.11, 138.01, 137.97, 137.40, 137.32, 134.58, 132.44, 132.39, 131.73,130.97, 130.73, 130.60, 127.11, 126.66, 126. 10, 125.83, 125.22, 125.01,124.63, 123.88, 123.14, 121.80, 121,71 120.68, 120.32, 119.77, 119.38,118.61, 117.46, 113.02, 112.95, 110.91, 110.67, 109.55, 109.44, 109.26,MS (API-) m/z: 789.8 [(M + H)-].

Reference： [1]Organic electronics,2017,vol. 42,p. 337 - 342

76
[ 18628-07-4 ]
[ 17654-70-5 ]
4,6-di(9H-[3,9'-bicarbazol]-9-yl)isophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: Sodium hydride (60% in oil, 0.16 g, 3.98 mmol) and 9H-3,9'-bicarbazole (0.85 g, 2.53 mmol) were stirred in 3 ml anhydrousDMF solvent under a nitrogen atmosphere. After 20 min, 4,5-difluorophthalonitrile (0.20 g, 1.21 mmol) in 5 ml DMF was addedthe mixture. The reaction mixture was stirred at room temperaturefor 1 h. The reaction mixture was quenched with distilled water.Organic layer of the mixture was extracted with dichloromethaneand distilled water. Then solvent of organic layer was evaporatedand purified by column chromatography (dichloromethane/nhexane).

Reference： [1]Organic electronics,2017,vol. 42,p. 337 - 342

77
2,5-difluoro-1,4-dicyanobenzene [ No CAS ]
[ 18628-07-4 ]
2,5-di(9H-[3,9'-bicarbazol]-9-yl)terephthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		General procedure: Sodium hydride (60% in oil, 0.16 g, 3.98 mmol) and 9H-3,9'-bicarbazole (0.85 g, 2.53 mmol) were stirred in 3 ml anhydrousDMF solvent under a nitrogen atmosphere. After 20 min, 4,5-difluorophthalonitrile (0.20 g, 1.21 mmol) in 5 ml DMF was addedthe mixture. The reaction mixture was stirred at room temperaturefor 1 h. The reaction mixture was quenched with distilled water.Organic layer of the mixture was extracted with dichloromethaneand distilled water. Then solvent of organic layer was evaporatedand purified by column chromatography (dichloromethane/nhexane).

Reference： [1]Organic electronics,2017,vol. 42,p. 337 - 342

78
[ 18628-07-4 ]
6-(9H-carbazol-9-yl)-9-(5-chlorobenzo[b]thiophen-3-yl)-9H-pyrido[2,3-b]indole [ No CAS ]
9-(3-(6-(9H-carbazol-9-yl)-9H-pyrido[2,3-b]indol-9-yl)benzo[b]thiophen-5-yl)-9H-3,9'-bicarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		In a 250 ml round bottom flask in the push, the 5 ml tetrahydrofuran (THF) is poured into the 9H-3,9 '-double-carbazole (0.1g, 3 . 0mmol) in. Furthermore, in the ice bath, the 2.5M n-butyl lithium/hexane solution (0.8 ml) in the mixture is gradually added. Under room temperature, stirring the mixture solution 30 minutes, then the 9 - (5-chlorobenzo thiophene-3-yl) oxazole (1.0g, 2 . 0mmol) and four (triphenylphosphine) palladium (0) (Pd (pph 3) 4) (0.020g) in solution is poured into the mixture, the resulting mixture is dissolved in tetrahydrofuran (THF), and the 80 C reaction. After the reaction, filtration and precipitation and by methylene chloride and methanol is recrystallized, therefore obtain 0.54g product (34%).

Reference： [1]Patent: CN103896967,2016,B .Location in patent: Paragraph 0070; 0071

79
[ 14348-75-5 ]
[ 18628-07-4 ]
C₆₁H₃₆N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate; In toluene; for 10h;Inert atmosphere; Reflux;	synthetic route:250mL three bottles,In the atmosphere of nitrogen gas,0.01 mol of 2,7-dibromo-9-fluorenone was added,0.025 mol of intermediate G1,0.04 mol of sodium tert-butoxide,1 x 10-4 mol Pd (dppf) Cl2,180 mL of toluene,Heated to reflux for 10 hours,Sampling point plate,Raw material reaction is complete;Natural cooling to room temperature (20 ~ 25 ),filter,The filtrate was collected and evaporated under reduced pressure (-0.09 MPa, 85 C)Column chromatography,Get the target product,HPLC purity 98.6%Yield 68.6%.

Reference： [1]Patent: CN106467484,2017,A .Location in patent: Paragraph 0099; 0100; 0101; 0102; 0103; 0104

80
[ 18628-07-4 ]
C₂₄H₂₁BBr₂ [ No CAS ]
C₇₂H₅₁BN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.8%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 20h;Reflux; Inert atmosphere;	250ml four bottles,Under nitrogen protection,0.025 mol of intermediate A was added,0.01 mol of 3-carbazolylcarbazole,0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,200 ml of toluene,Heated to reflux for 20 hours,The reaction is complete;Natural cooling,filter,The filtrate is steamed,Over silica gel column,With a toluene: ethanol = 3: 1 (volume ratio) mixed solvent beating,After recrystallization, the white solid,Purity (HPLC) was 98.55%Yield 65.8%.

Reference： [1]Patent: CN106467554,2017,A .Location in patent: Paragraph 0112; 0113; 0114; 0115; 0116; 0117; 0118

81
[ 57102-42-8 ]
[ 18628-07-4 ]

Reference： [1]Patent: CN106661001,2017,A

82
[ 95-51-2 ]
[ 18628-07-4 ]

Reference： [1]Patent: CN106661001,2017,A

83
C₂₄H₁₇ClN₂ [ No CAS ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrafluoroboric acid; tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; In N,N-dimethyl acetamide; at 180℃; for 24h;	Compound J78 can be synthesized by a person of ordinary skill following Scheme 1 illustrated in FIG. 2. The starting material Sl-1 is available for purchase from Alfa Aesar (CAS No. 57102-42-8). The starting material SI -2 is available for purchase from Acros Organics (CAS No. 95-51-2). In the first step compound Sl-1 is combined with compound S I -2, potassium tert-butoxide, Pd(OAc)2, and PtBu3 in toluene at 120 C for 24 hours to form compound S I -3. In the second step, compound S I -3 is combined with potassium carbonate, Pd(OAc)2, and PtBu3HBF4, in DMA at 180 C for 24 hours to form compound S I -4. In the third step, compound SI -4 is combined with compound S 1-5 (available for purchase from Acros Organics, CAS No. 589-87-7), K3P04 and copper iodide in toluene at 80 C for 10 minutes to form compound SI -6. In the fourth step, compound SI -6 is cooled to 0 C in a hexanesxyclopentylmethyl ether solution before dropwise addition of nBuLi and subsequent dropwise addition of Bu3SnCl to form compound S l-7. Compound Sl-7 is combined with compound S I -8 (available for purchase from Tokyo Chemical Industry Co., CAS No. 3740- 92-9) with Pd(OAc)2 to form compound J78. It is understood that steps 1, 2, 3, 4, and 5 can be performed and optimized by a person having ordinary skill in the art without undue experimentation.

Reference： [1]Patent: CN106661001,2017,A .Location in patent: Paragraph 0339; 0340; 0392; 0393

84
[ 18628-07-4 ]
C₄₂H₄₆N₂Sn [ No CAS ]

Reference： [1]Patent: CN106661001,2017,A

85
[ 589-87-7 ]
[ 18628-07-4 ]
9-(4-bromophenyl)-9H-3',9'-dicarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene;Reflux;	8.2 g of 4-Bromoiodobenzene (SM A1) in a round bottom flask,10 g of 3,9'-bicarbazole (SM B1), 5.8 g t-BuONa, 0.8 g Pd 2 (dba) 3,1.6 ml of (t-Bu) 3 P was dissolved in 70 ml of toluene and stirred under reflux.The reaction was confirmed by TLC and the reaction was terminated after the addition of water.The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column purification and recrystallization.12.1 g (yield 81%) of 9- (4-Bromophenyl) -9H-3,9'-bicarbazole (Sub C1) was obtained.
70%	With potassium phosphate; copper(l) iodide; In 1,4-dioxane; at 90℃; for 15h;Inert atmosphere;	Under a nitrogen atmosphere (N2 purging), Compound 2A(10 g, 35.48 mmol), 0.6 equivalent of Compound 4A, 0.1 equivalent of CuI, 3.5 equivalents of diaminocyclohexane, and 4.0 equivalents of potassium phosphate were added to 1,4-dioxane(350 ml), and stirred in a 90 C. oil bath. After 15 hours, water was added to the reaction mixture, and extraction was performed. Then, purification was performed using a column using a developing solvent of hexane: MC (3:2) to obtain a white solid 4B(12.07 g, yield 70%).
	With potassium phosphate; copper(l) iodide; In toluene; at 80℃; for 0.166667h;	Compound J78 can be synthesized by a person of ordinary skill following Scheme 1 illustrated in FIG. 2. The starting material Sl-1 is available for purchase from Alfa Aesar (CAS No. 57102-42-8). The starting material SI -2 is available for purchase from Acros Organics (CAS No. 95-51-2). In the first step compound Sl-1 is combined with compound S I -2, potassium tert-butoxide, Pd(OAc)2, and PtBu3 in toluene at 120 C for 24 hours to form compound S I -3. In the second step, compound S I -3 is combined with potassium carbonate, Pd(OAc)2, and PtBu3HBF4, in DMA at 180 C for 24 hours to form compound S I -4. In the third step, compound SI -4 is combined with compound S 1-5 (available for purchase from Acros Organics, CAS No. 589-87-7), K3P04 and copper iodide in toluene at 80 C for 10 minutes to form compound SI -6. In the fourth step, compound SI -6 is cooled to 0 C in a hexanesxyclopentylmethyl ether solution before dropwise addition of nBuLi and subsequent dropwise addition of Bu3SnCl to form compound S l-7. Compound Sl-7 is combined with compound S I -8 (available for purchase from Tokyo Chemical Industry Co., CAS No. 3740- 92-9) with Pd(OAc)2 to form compound J78. It is understood that steps 1, 2, 3, 4, and 5 can be performed and optimized by a person having ordinary skill in the art without undue experimentation.

With potassium phosphate; copper(l) iodide; In 1,4-dioxane; at 90℃; for 12h;

In the nitrogen environment (N2 purging), 7A,0.6 equivalent of 2A, 0.1 equivalent of CuI,3.5 equivalents of diaminocyclohexane, 4.0 equivalents of potassium phosphate were added to 1,4-dioxaneAnd stirred in an oil bath at 90 C.Water was added to the reaction mixture after 12 hours, and after extraction, white solid 7B was obtained after column using Hexane: MC (4: 1) developing solvent.

Reference： [1]Patent: KR2019/79765,2019,A .Location in patent: Paragraph 0107-0110
[2]Patent: US2018/166636,2018,A1 .Location in patent: Paragraph 0131; 0132
[3]Patent: CN106661001,2017,A .Location in patent: Paragraph 0339; 0340; 0392; 0393
[4]Patent: KR2019/27540,2019,A .Location in patent: Paragraph 0175; 0176-0178

86
[ 18628-07-4 ]
C₂₆H₁₆BrN₅ [ No CAS ]
C₅₀H₃₁N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 24h;Reflux;	2.0 g (4.18 mmol) of bromo compound, 1.67 g (5.02 mmol) of 3-carbazolyl-carbazole, 0.040 g (0.21 mmol) of copper(l) iodide, 0.05 ml (0.42 mmol) of trans-1 ,2-cyclohexanediamine and 1.01 g (8.36 mmol) of tripotassium phosphate in 70 ml of 1 ,4-dioxane are reflux for 24 h. The reaction mixture is cooled at room temperature and added 30 ml of 1 N aqueous hydrochloric acid. The inorganic solids are filtered, then the filtrate is extracted with di- chloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. Gradient column chromatography on silica gel with dichloromethane/ethyl acetate (di- chloromethane100%, 95/5) gives the product. Yield 2.1 g (69 %). 1 H NMR (400 MHz, CDCI3): delta 8.27 (d, J = 1.9 Hz, 1 H); 8.23 - 8.16 (m, 4H); 8.10 (d, J 7.6 Hz, 1 H); 8.04 - 7.98 (m, 2H); 7.87 - 7.81 (m, 2H); 7.72 - 7.60 (m, 7H); 7.56 - 11 (m, 2H); 7.49 - 7.44 (m, 1 H); 7.44 - 7.34 (m, 8H); 7.33 - 7.26 (m, 3H).

Reference： [1]Patent: WO2017/178864,2017,A1 .Location in patent: Page/Page column 88-89

87
[ 18628-07-4 ]
C₂₆H₁₆IN₅ [ No CAS ]
C₅₀H₃₁N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 24h;Reflux;	Example 20 O g (14.3 mmol) of iodo compound, 5.69 g (17.1 mmol) of 3-carbazolyl-carbazole, 0.136 g (0.71 mmol) of copper(l) iodide, 0.2 ml (1.43 mmol) of trans-1 ,2-cyclohexanediamine and 3.46 g (28.6 mmol) of tripotassium phosphate in 200 ml of 1 ,4-dioxane are reflux for 24 h. The reaction mixture is cooled at room temperature and added 100 ml of 1 N aqueous hydrochloric acid. The inorganic solids are filtered, then the filtrate is extracted with di- chloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. Gradient column chromatography on silica gel with dichloromethane/ethyl acetate (di- chloromethane100%, 95/5) gives the product. Yield 9.90 g (95 %). 1H NMR (400 MHz, CDCI3): delta 8.33 (d, J = 1.9 Hz, 1 H); 8.26 - 8.13 (m, 5H); 7.97 (d, J = 8.2 Hz, 2H); 7.89 (dd, J = 8.6, 2.2 Hz, 1 H); 7.82 - 7.72 (m, 4H); 7.67 - 7.61 (m, 3H); 7.57 (t, J = 7.6 Hz, 1 H); 7.51 (t, J = 7.9 Hz, 2H); 7.45 - 7.27 (m, 12H).

Reference： [1]Patent: WO2017/178864,2017,A1 .Location in patent: Page/Page column 91

88
[ 18628-07-4 ]
C₂₀H₁₁IN₄S [ No CAS ]
C₄₄H₂₆N₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 24h;Reflux;	Example 33 2.72 g (5.83 mmol) of bromo-iodo compound, 2.33 g (7.00 mmol) of 3-carbazolyl-carbazole, 0.056 g (0.29 mmol) of copper(l) iodide, 0.07 ml (0.58 mmol) of trans- 1 ,2- cyclohexanediamine and 1.41 g (1 1.7 mmol) of tri potassium phosphate in 100 ml of 1 ,4- dioxane are reflux for 24 h. The reaction mixture is cooled at room temperature and added 50 ml of 1 N aqueous hydrochloric acid. The inorganic solids are filtered, then the filtrate is extracted with dichloromethane. The organic layer is dried over sodium sulfate and concentrated in vacuo. Gradient column chromatography on silica gel with dichloromethane/ethyl acetate (dichloromethane100%, 95/5) gives the product. Yield 4.3 g (93 %). 1H NMR (400 MHz, CDCI3): delta 8.34 (d, J = 1 .9 Hz, 1 H); 8.25 - 8.14 (m, 5H); 8.03 (dd, J = 8.4, 2.4 Hz, 1 H); 7.89 (d, J = 7.5 Hz, 1 H); 7.87 - 7.83 (m, 1 H); 7.80 (d, J = 8.7 Hz, 1 H); 7.71 (d, J = 7.8 Hz, 1 H); 7.69 - 7.64 (m, 2H); 7.64 - 7.55 (m, 2H); 7.48 - 7.39 (m, 7H); 7.38 - 7.29 (m, 4H).

Reference： [1]Patent: WO2017/178864,2017,A1 .Location in patent: Page/Page column 98

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	18628-07-4	MDL No. :	MFCD27644690
Formula :	C₂₄H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FHJJVSJWFYYPAC-UHFFFAOYSA-N
M.W :	332.40	Pubchem ID :	13236022
Synonyms :

Num. heavy atoms :	26
Num. arom. heavy atoms :	26
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	110.14
TPSA :	20.72 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.74 cm/s

Log Po/w (iLOGP) :	3.04
Log Po/w (XLOGP3) :	6.46
Log Po/w (WLOGP) :	6.42
Log Po/w (MLOGP) :	5.02
Log Po/w (SILICOS-IT) :	5.58
Consensus Log Po/w :	5.3

[ CAS No. 18628-07-4 ] {[proInfo.proName]}

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Water Solubility

Medicinal Chemistry

Safety of [ 18628-07-4 ]

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[ 18628-07-4 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-6.64
Solubility :	0.0000753 mg/ml ; 0.000000227 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.69
Solubility :	0.0000679 mg/ml ; 0.000000204 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.18
Solubility :	0.000000218 mg/ml ; 0.0000000007 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.07

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

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P103	Read label before use
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Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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Code	Phrase
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P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling