56525-79-2|3,6-Diphenyl-9H-carbazole| Ambeed

Structure of 56525-79-2

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Quality Control of [ 56525-79-2 ] Purity: 98% SDS Specification

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Product Details of [ 56525-79-2 ]

CAS No. :	56525-79-2
Formula :	C₂₄H₁₇N
M.W :	319.40
SMILES Code :	C1(NC2=C3C=C(C4=CC=CC=C4)C=C2)=C3C=C(C5=CC=CC=C5)C=C1
MDL No. :	MFCD00222619
InChI Key :	PCMKGEAHIZDRFL-UHFFFAOYSA-N
Pubchem ID :	3123295

Safety of [ 56525-79-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 56525-79-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	25
Num. arom. heavy atoms	25
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	106.68
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	15.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	6.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.66
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.24
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	6.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.61
Solubility	0.0000781 mg/ml ; 0.000000245 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.77
Solubility	0.0000539 mg/ml ; 0.000000169 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-9.97
Solubility	0.0000000341 mg/ml ; 0.0000000001 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.53 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.03

Application In Synthesis of [ 56525-79-2 ]

* 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.

Downstream synthetic route of [ 56525-79-2 ]

[ 56525-79-2 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 80℃; for 5h;	General procedure: Intermediates 2 (5g, 13.7mmol) and the intermediate body 4 (7.2g, 16.4mmol), sodium carbonate (7.2g, 68.3mmol), 200 ml toluene, multi function cap a 100 ml distilled 20 minutes in 80 °C paste has better mouth feeling and heating stirring section. [...] tetra herein (0.79g, 0.68mmol) added of after, the reflux heating at a 5 stirring section. Reactants after cooled down to the normal temperature, separation of is layer was taken. Organic layer is concentrated under the silica gel column chromatography purified, 7g a 2 (formula 2) drying the compounds obtained (yield 75percent). Derivatives, HR-MS, 1 H NMR, 13 C NMR the, identified through use of a.
67.9%	With triethyl phosphite; for 12h;Inert atmosphere; Reflux;	General procedure: Under nitrogen, taken 22.0g (0.08) mol of intermediate A, 66.4g (0.4mol) of triethyl phosphite, placed in three250mL round bottom flask, under magnetic stirring at reflux for 12h after distillation under reduced pressure toremove excess alkylene triethylphosphite was cooled to room temperature, filtered, solid was H 2 O, washed withethanol several times, dried, and weighed to give 2-phenyl--9H- carbazole 14.3g. Yield 73.6percent.A

2
[ 56525-79-2 ]
[ 501330-43-4 ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 1140 - 1141.
[3]Tetrahedron,2010,vol. 66,p. 7707 - 7719.

3
[ 57103-02-3 ]
[ 98-80-6 ]
[ 56525-79-2 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 1140 - 1141.
[2]Heterocycles,2007,vol. 72,p. 133 - 138.
[3]Tetrahedron,2010,vol. 66,p. 7707 - 7719.

4
[ 19802-70-1 ]
[ 56525-79-2 ]
2,3-bis[4-(3,6-diphenylcarbazol-9-yl)pbenyl]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate;palladium diacetate; tri-tert-butyl phosphine; In hexane; xylene; at 130℃; for 12h;	[Step 3] A synthesis method of 2,3-bis[4-(3,6-diphenylcarbazol-9-yl)pbenyl]quinoxaline (DPCPQ) is described. A synthesis scheme of DPCPQ was represented by (a-3). [Show Image] 2.3g of 2,3-bis(4-bromophenyl)quinoxaline (6.1 mmol), 4.3 g of 3,6-diphenyl carbazole (14 mmol), 0.061g of palladium(II) acetate (0.27 mmol), 5.6 g of potassium carbonate (41 mmol) were put into a 200 mL three-necked flask, and the inside was substituted by nitrogen. Into this mixture, 50 mL of xylene, and 1.7 g of tri(tert-butyl)phosphine (10 percent hexane solution) (0.81 mmol) were added. This mixture was stirred for 12 hours at 130 °C. After the reaction, a precipitate of the reaction mixture was filtrated by suction to be collected. The obtained solid was dissolved in chloroform and this solution was filtrated by suction through Florisil, celite, and alumina. The filtrate was condensed, the obtained solid was recombined with a mixed solvent of chloroform and hexane to be recrystallized and 3.2 g of an objective matter, a lemon-yellow powder solid was obtained at the yield 57 percent. It was confirmed by a nuclear magnetic resonance method (NMR) that this compound was DPCPQ. 3.2 g of the obtained DPCPQ was refined by sublimation at 380 °C under the following conditions: the pressure was 5.6 Pa, and an argon flow rate was 3.0 mL/min. 0.8 g of DPCPQ was collected and the collection rate was 25 percent. The analysis result of DPCPQ by proton nuclear magnetic resonance spectrometry (1HNMR) was as follows. 1HNMR (CDCl3, 300 MHz): delta =7.32-7.37 (m, 4H), 7.42-7.47 (m, 8H), 7.57-7.60 (m, 4H), 7.69-7.81 (m, 17H), 7.88-7.94 (m, 6H), 8.29-8.32 (m, 2H), 8.42-8.42 (m, 3H). FIG 8A is a 1HNMR chart of DPCPQ, and FIG. 8B is an enlarged 1HNMR chart of DPCPQ in 7.0 to 9.0 ppm.

References: [1]Patent: EP1905768,2008,A1 .Location in patent: Page/Page column 36.

5
[ 56525-79-2 ]
(4S,4'S)-2,2'-(3,6-diphenyl-9H-carbazole-1,8-diyl)bis(4-isopropyl-4,5-dihydrooxazole) [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.
[2]Heterocycles,2007,vol. 72,p. 133 - 138.
[3]Journal of the American Chemical Society,2003,vol. 125,p. 1140 - 1141.

6
[ 56525-79-2 ]
C₂₈H₂₁NO₄ [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

7
[ 56525-79-2 ]
[ 943786-98-9 ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

8
[ 56525-79-2 ]
[ 943787-00-6 ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

9
[ 56525-79-2 ]
[ 943787-02-8 ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

10
[ 56525-79-2 ]
C₃₆H₃₅N₃O₂ [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

11
[ 56525-79-2 ]
1,8-dicyano-3,6-diphenyl-carbazole [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 1140 - 1141.

12
[ 56525-79-2 ]
(4S,4'S)-2,2'-(3,6-diphenyl-9H-carbazole-1,8-diyl)bis(4-methyl-4,5-dihydrooxazole) [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.
[2]Heterocycles,2007,vol. 72,p. 133 - 138.

13
[ 56525-79-2 ]
1,8-bis((S)-4-tert-butyl-4,5-dihydrooxazol-2-yl)-3,6-diphenyl-9H-carbazole [ No CAS ]

References: [1]Heterocycles,2007,vol. 72,p. 133 - 138.

14
[ 56525-79-2 ]
[ 3001-15-8 ]
[ 524067-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; copper(II) sulfate; In tridecane; at 230℃; for 24h;	(Compound 1): In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane.. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours.. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water.. The solid resulting was then dissolved in hot toluene.. The insoluble residue was filtered hot.. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder.. This compound had a melting point of 294° C.

References: [1]Patent: US6670054,2003,B1 .Location in patent: Page column 28-29.

15
[ 6825-20-3 ]
[ 98-80-6 ]
[ 56525-79-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere;	It was dissolved in 3,6-dibromo-9H-carbazole(100 g, 308 mmol) in a nitrogen environment in 700 mL tetrahydrofuran(THF), here the phenylboronic acid(45.1 g, 370 mmol) and put tetrakis(triphenylphosphine) palladium (10.7 g, 9.24mmol) was stirred. Into a potassium carbonate (213 g, 1,540 mmol) in a saturated water was heated to reflux at 80 C for 16 hours. After the reaction was completed, the reaction solution into water and extracted with DCM then water was removedwith anhydrous MgSO4, filter and was concentrated under reduced pressure. Thus the resulting residue was separated and purified by flash column chromatography to obtain the compound I-23(74.8 g, 76%).
75%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; In water; toluene;Inert atmosphere; Reflux;	Synthesis of 3,6-diphenyl-9H-carbazole 3,6-Dibromo-9H-carbazole (10.0 g, 30.8 mmol), phenylboronic acid (8.25 g, 67.7 mmol) Pd2(dba)3 (0.564 g, 0.615 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhOS) (1.011 g, 2.462 mmol), and potassium phosphate hydrate (28.3 g, 123 mmol) were dissolved in the mixture of toluene (350 mL) and water (40 mL) in a three-necked flask. The mixture was degassed by bubbling nitrogen, then it washeated to reflux overnight. After completion of the reaction, the mixture partitioned between ethyl acetate and water. The aqueous layer was washed 3 times with ethyl acetate and the combined organic layers were washed with brine and water. The crude compound was purified by column chromatography on silica gel, eluted with hexane/DCM 1/1 (v/v) mixture. The target compound was obtained as a white solid (7.4 g, 75 % yield).
75.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 120℃;	3,6-dibromo-9H-carbazole (5 g, 15.3 mmol) and phenylboronic acid (5.63 g, 46.15 mmol) was dissolved in tetrahydrofuran (THF) (60 ml) into a 2-necked round bottom flask, Tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4) (0.89 g, 0.77 mmol), K2CO3 (8.3 g) was dissolved in distilled water (30 ml) at 2M, and the mixture was stirred at 120 C. Then, after the reaction was completed, the reaction product was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrated reaction product was purified by silica gel column chromatography to obtain 3.7 g of 3,6-diphenyl-9H-cabazole (hereinafter referred to as Sub 2) (yield: 75.5%).

74%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran;Inert atmosphere; Reflux;	Example 10; a) 3.09 g (9.23 mmol) of 3,6-dibromocarbazole and 2.78 g (22.2 mmol) of phenylboronic acid are stirred in 140 ml of THF under argon. 12.76 g (92.30 mmol) of potassium carbonate in 46 ml of water are added. 0.27 g (0.23 mmol) of palladium tetrakis(triphenylphosphine) are added under argon and the reaction is stirred under reflux over night. At room temperature, a 1 % aqueous solution of NaCN is added to the medium which is boiled for 20 min. At room temperature, ethyl acetate is added and the organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude material is purified by chromatography over silica gel (cyclohexane/ethyl acetate 4:1 ) to give 2.17 g of a white solid (74%). 1H NMR (CDCI3, 300 MHz) 8.34 (d, J = 1.8 Hz, 2H), 8.11 (s, 1 H), 7.74- 7.68 (m, 6H), 7.52-7.45 (m, 6H), 7.37-7.32 (m, 2H).
74%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 80℃; for 8h;Inert atmosphere;	In the nitrogen atmosphere, 3,6-dibromocarbazole (5 g, 15.4 mmol) was added sequentially to the flask, Phenylboronic acid (4.1 g, 33.9 mmol) (Triphenylphosphine) palladium (0.7 g, 0.6 mmol) Toluene (45 ml), 2M sodium carbonate (45 ml), And the mixture was stirred at 80 C for 8 hours. After separating the organic phase, Concentrated under reduced pressure in an evaporator. The resulting residue was purified by silica gel column chromatography, 3,6-diphenylcarbazole (3.6 g, yield 74%) was obtained.
74%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 80℃; for 8h;Inert atmosphere;	In the nitrogen atmosphere,3,6-dibromocarbazole (5 g, 15.4 mmol) was added sequentially to the flask,Phenylboronic acid (4.1 g, 33.9 mmol)(Triphenylphosphine) palladium (0.7 g, 0.6 mmol)Toluene (45 ml),2M sodium carbonate (45 ml),And stirred at 80 C for 8 hours.After separating the organic phase,Concentrated under reduced pressure in an evaporator.The resulting residue was purified by silica gel column chromatography,3,6-diphenylcarbazole (3.6 g, yield 74%) was obtained.
73%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 10h;Heating / reflux;	Preparation of 3,6-diphenylcarbazole Reaction 5As depicted in Reaction 5, 15g (46 mmol) of 3,6-dibromocarbazole, 14g (92 mmol) of phenylboronic acid, K2CO3 (2 mol), Pd(PPh3)4 and toluene were refluxed for 10 hours. The reaction mixture was extracted with methylene chloride. The solvent was removed, and then the residue was purified by column chromatography (eluent: hexane) to give the title compound. Yield: 73%. MS (El) (Calcd. for C24H17N: 319.14, Found: 319).
69%	With palladium diacetate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; water;Reflux;	First, 100 g (310 mmol) of 3,6-dibromocarbazole (CAS 6825-20-3) E1 together with 189 g (1550 mmol) of phenylboronic acid (CAS 98-80-6) E2And 430 g (3.1 mol) of potassium carbonate was introduced into a 41 four-necked flask and dissolved in 1000 ml of tetrahydrofuran and 300 ml of water.After the mixture had been degassed for 30 minutes, 140 mg (0.62 mmol) of palladium acetate and 650 mg of triphenylphosphine were added, and the mixture was heated overnight under reflux.700 ml of water was then added to the batch and the aqueous phase was extracted several times with dichloromethane.The combined organic phases were dried over sodium sulfate and the solvent mixture was removed in vacuo.The resulting residue was dissolved in 1.5 mL of dichloromethane and filtered.The solvent was again removed in vacuo and the solid was washed with stirring with 600 mL of ethanol.Filtration and drying gave 68 g (0.21 mol, 69%) of desired material.
68%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃;	Carbazole (16.72g, 100mmol), NBS (59.4g, 210mmol), BPO (2.42g, 10mmol), methylene chloride (300 ml) at room temperature is injected into the medal and then 2000. When reaction is completed methylene chloride and water, NaHCO 3 extracted using aqueous solution obtained after the organic layer Na 2 SO 4 dried to, for the products and re-crystallized concentrating 23.73g (73%)obtained. Said product obtained (23.73g, 73.02mmol), phenylboronic acid (19.6g, 160.64mmol), Pd (PPh 3) 4, (8.44g, 7.3mmol), K 2 CO 3 (60.55g, 438.12mmol), THF (320 ml), water (160 ml) in 80 C agitation return current doesn't have any error frames, turns on the light. When reaction is completed for reducing temperature a high temperature to the normal temperature after methylene chloride and a water extraction of the organic layer obtained after MgSO 4 dried to, for the products and re-crystallized concentrating 15.9g (68%)obtained
63%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 3.5h;	As an example of a material according to the invention, a synthetic method of a compound represented by formula (59) 9-[4-(3, 6-diphenyl-N-carbazolyl)] phenyl- 10-phenylanthracene (hereinafter referred to as DPCzPA) below will be described. [0209][0210] This compound is prepared in accordance with the synthetic method shown below. Note that 9-phenyl-10-(4-bromophenyl) anthracene is prepared in the manner shown in Example 1. [0211]First, a synthetic method of 3,6-dibromocarbazole will be shown below. A mixture of 6.5 g (20.0 mmol) 3,6-dibromocarbazole, 5.0 g (41.0 mmol) of phenylboronic acid, 93 mg (0.40 mmol) of palladium acetate, 6.9 g (5.2 mmol) of potassium carbonate, water (25 mL), 610 mg of tri(ortho-tolyl) phosphine, and dimethoxyethane (50 mL) is heated to reflux at 80 0C for 3.5 three hours. After the reaction, the solution is rinsed with water, aqueous layer is extracted with toluene, and it is rinsed together with the organic layer using saturated salt solution, and thereafter EPO <DP n="67"/>dried with magnesium sulfate. After natural filtration, the filtrate is condensed to obtain 4.1 g of 3,6-di(2-phenyl-phenyl)-carbazoleas a white solid at a yield of 63 %. A synthetic scheme of 3,6-di(2-phenyl-phenyl)-carbazoleis shown below.
63%	With potassium carbonate;palladium diacetate; Tri(p-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 3.5h;	[Step 2] A synthesis method of 3,6-diphenylcarbazole is described.; A synthesis scheme of 3,6-diphenylcarbazole is represented by (a-2). [Show Image] 6.5 g of 3,6-dibromocarbazole (20 mmol), 5.0 g of phenylboron acid (41 mmol), 93mg of palladium(II) acetate (0.40 mmol), 610mg of tri(ortho-tolyl)phosphine (1.9mmol) were put into a 200mL three-necked flask, and then, the inside of the flask was substituted by nitrogen. Into the mixture, 50 ml of ethyleneglycol dimethylether (abbreviation : DME), and 25 mL of a pottassium carbonate water solution (2.0 mol/L) were added. This mixture was refluxed for 3.5 hours at 80 C. After the reaction, the reaction mixture was washed with water and a water layer was extracted with toluene. The extracted solution and an organic layer were washed with a saturated saline, and dried by magnesium sulphate. The mixture was naturally filtrated. The filtrate was condensed, and 4.1 g of an objective matter, a white powder solid was obtained at the yield 63 %.
63%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 17h;Inert atmosphere;	A mixture of 3,6-dibromo-9H- carbazole (3.0 g, 9.2 mmol) (Aldrich), phenylboronic acid (3.0 g, 25 mmol) (Aldrich), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.3 g, 0.26 mmol) (Frontier Scientific, Logan, UT) and potassium carbonate (6.5 g, 47 mmol) (Aldrich) in dioxane/water (75 mL/15 mL) (Aldrich) was degassed with bubbling argon (Airgas, San Marcos, CA) for 60 min and heated at about 100 C on a hot plate with a silicone oil bath for about 16 hours. Upon cooling to room temperature, the whole mixture was mixed with ethyl acetate (Aldrich) and rinsed with brine. Then, the organic mixture was dried over Na2S04 (Aldrich), loaded on silica gel (Grade 135) and purified by flash column using eluents of ethyl acetate/hexanes (10% to 30%) (Aldrich). After removal of solvents, a white solid (Compound OSC-3) was obtained (2.1 g, in 63% yield). Confirmed by 1 HNMR (Jeol Instruments, Peabody, MA).
63%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;	A mixture of 3,6-dibromo-9H-carbazole (3.0 g, 9.2 mmol), phenylboronic acid (3.0 g, 25 mmol), Pd(PPh3)4 (0.3 g, 0.26 mmol) and potassium carbonate (6.5 g, 47 mmol) in dioxane/water (75 mL/15 ml) was degassed and heated at about 100 C for about 16 hours. Upon cooling to room temperature, the whole was worked up with ethylacetate/brine, the organic was dried over Na2So4, loaded on silica gel and purified by flash column using eluents of ethyl acetate/hexane (10% to 30%). After removal of solvents, a white solid (Compound 11 ) was obtained (2.1 g, in 63% yield).
48%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 10h;Inert atmosphere;	30 g (92.3 mmol) of 3,6-dibromo-9H-carbazole was dissolved in 0.3 L of tetrahydrofuran (THF) in a nitrogenenvironment, 28 g (231 mmol) of phenyl boronic acid and 3.2 g (2.8 mmol) of tetrakis(triphenylphosphine)palladium wereadded thereto, and the mixture was agitated. 40.8 g (277 mmol) of potassium carbonate saturated in water was addedthereto, and the mixture was heated and refluxed at 80 C for 10 hours. When the reaction was terminated, water wasadded to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrousMgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. The obtained residue wasseparated and purified through flash column chromatography, obtaining a compound I-4 (14.3 g, 48 %). HRMS (70 eV, EI+): m/z calcd for C24H17N: 319.1361, found: 319.1. HRMS (70 eV, EI+): m/z calcd for C24H17N: 319.1361, found: 319.1.
33%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 4h;Inert atmosphere;	General procedure: Under nitrogen protection system, 3-bromo -9H- carbazole 1.6mmol, tetrakistriphenylphosphine palladium 0.64mmol, anhydrous carbonatePotassium1.92mmol phenylboronic acid 1.92mmol, was dissolved in N, N- dimethylformamide: H2O = (15ml: 2ml) mixed solvent,80 stirring for 4h, after completion of the reaction, cooled to room temperature, the mixed solution was extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesiumDried and evaporated, evaporated and the product after column chromatography to obtain 3-phenyl -9H- carbazole (A-1) 1.44mmol, 90% yield. The method of the same A-1, by column chromatography to obtain a white solid product 3,6-diphenyl -9H- carbazole (A-2), producingRate of 33%.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 18h;Heating / reflux;	EXAMPLE I Synthesis of 3,6-diphenyl carbazole In a 250 milliliter round bottom flask there were added 3,6-dibromocarbazole (5 grams), 50 milliliters of 1,2-dimethoxyethane, phenylboric acid (4.8 grams) dissolved in ethanol, and sodium carbonate (4.2 grams) dissolved in 20 milliliters of water.. After the resulting solution was saturated with argon, 0.49 gram of tetrakis-(triphenylphosphine) palladium was added.. The reaction mixture was heated to reflux and stirred for 18 hours.. The reaction flask was removed from the heat and cooled to room temperature, about 22 C. to about 25 C. The resulting solution was transferred to a separatory funnel, and the organic layer, which contained product, was separated from the aqueous phase.. After removal of the organic solvents by evaporation, the residue was subjected to column chromatography on silica gel to yield 3.5 grams of 3,6-diphenyl carbazole as colorless powder product.. Its chemical structure was confirmed by Proton IR analysis.
		According to an ordinary process, 3,6-diphenylcarbazole was synthesized by reacting 3,6-dibromocarbazole and phenylboronic acid.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene;	Manufacturing Example 8 A solution was prepared by adding 12.7 g of 3,6-dibromocarbazole, 10.0 g of phenylboronic acid, and 2.61 g of tetrakis(triphenylphosphine)palladium into 40 ml of ethanol and 170 ml of toluene. The resulting solution was blended with 90 ml of a 22% aqueous solution of sodium carbonate, and the mixture was heated under reflux in a nitrogen atmosphere for 5 hours. Insoluble materials were removed therefrom by performing hot filtration using a filter aid. Thereafter, the organic layer was separated from the aqueous layer, and the solvent was distilled off under a reduced pressure. After washing with water and drying were performed, a light brown powder was prepared. The resulting powder was subjected to a column chromatography treatment (eluant: toluene), followed by washing with hexane. Thus, 6.0 g of a colorless needle crystal of 3,6-diphenylcarbazole was produced. The physical properties thereof were as follows. melting point: 180.5 C. to 181.5 C. elemental analysis value (%): measured value/calculated value C 90.44/90.24 H 5.25/5.38 N 4.31/4.39 infrared absorption spectrum (KBr pellet method) NH stretching vibration: 3423, 3378 cm-1
38 g		3,6-dibromocarbazole (50 g, 0.154 mol), phenylboronic acid (41 g, 0.336 mol), 150ml water, 80g sodium carbonate, and 600ml dioxane were charged into a 2 liter pot with magnetic stirrer, reflux condenser and nitrogen inlet, and sparged with nitrogen for one hour. Pd2DBA3 (6g, 0.0066mol) and tri-t-butylphosphine (3 g, 0.0148mol) was quickly added from the drybox. The reaction was refluxed overnight. The next day water was added to the reaction mixture and methylene chloride extractions were preabsorbed to 141 g of activated silica and purified by column chromatography using methylene chloride/hexanes yielding 38 grams of product 3,6-diphenylcarbazole.

References: [1]Patent: KR2015/6758,2015,A .Location in patent: Paragraph 0362-0364.
[2]Patent: EP2818468,2014,A2 .Location in patent: Paragraph 0102; 0103.
[3]Patent: KR2019/31734,2019,A .Location in patent: Paragraph 0092-0096.
[4]Patent: WO2010/46259,2010,A1 .Location in patent: Page/Page column 55.
[5]Patent: TWI554499,2016,B .Location in patent: Page/Page column 89.
[6]Patent: TW2016/38086,2016,A .Location in patent: Page/Page column 41; 42.
[7]Patent: WO2008/120899,2008,A1 .Location in patent: Page/Page column 29.
[8]Patent: TWI633106,2018,B .Location in patent: Page/Page column 47.
[9]Patent: KR2015/115226,2015,A .Location in patent: Paragraph 0158; 0159; 0160.
[10]Patent: WO2006/104221,2006,A1 .Location in patent: Page/Page column 63-64.
[11]Patent: EP1905768,2008,A1 .Location in patent: Page/Page column 36.
[12]Patent: WO2015/195837,2015,A1 .Location in patent: Paragraph 0060.
[13]Patent: JP2016/526025,2016,A .Location in patent: Paragraph 0104; 0123.
[14]Patent: EP2889296,2015,A1 .Location in patent: Paragraph 0168-0171.
[15]Journal of the American Chemical Society,2017,vol. 139,p. 4559 - 4567.
[16]Patent: CN105906547,2016,A .Location in patent: Paragraph 0139; 0140; 0141; 0142; 0143; 0144.
[17]Patent: US6670054,2003,B1 .Location in patent: Page column 27.
[18]Patent: EP1820801,2007,A1 .Location in patent: Page/Page column 89.
[19]Patent: US2005/84711,2005,A1 .
[20]Patent: WO2013/142633,2013,A1 .Location in patent: Paragraph 28; 29.
[21]Dyes and Pigments,2019,vol. 164,p. 390 - 397.

16
copper(ll) sulfate pentahydrate [ No CAS ]
[ 56525-79-2 ]
[ 629-50-5 ]
[ 3001-15-8 ]
[ 584-08-7 ]
[ 524067-29-6 ]
4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE II Synthesis of 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water. The solid resulting was then dissolved in hot toluene. The insoluble residue was filtered hot. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder. This compound had a melting point of 294° C. Its chemical structure was confirmed by proton analysis.

References: [1]Patent: US6562982,2003,B1 .

17
[ 110-71-4 ]
[ 6825-20-3 ]
[ 98-80-6 ]
[ 56525-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In ethanol; water;	EXAMPLE I Synthesis of 3,6-Diphenyl Carbazole In a 250 milliliter round bottom flask there were added 3,6-dibromocarbazole (5 grams), 50 milliliters of 1,2-dimethoxyethane, phenylboric acid (4.8 grams) dissolved in ethanol, and sodium carbonate (4.2 grams) dissolved in 20 milliliters of water. After the resulting solution was saturated with argon, 0.49 gram of tetrakis-(triphenylphosphine) palladium was added. The reaction mixture was heated to reflux and stirred for 18 hours. The reaction flask was removed from the heat and cooled to room temperature, about 22° C. to about 25° C. The resulting solution was transferred to a separatory funnel, and the organic layer, which contained product, was separated from the aqueous phase. After removal of the organic solvents by evaporation, the residue was subjected to column chromatography on silica gel to yield 3.5 grams of 3,6-diphenyl carbazole as colorless powder product. Its chemical structure was confirmed by Proton IR analysis.

References: [1]Patent: US6562982,2003,B1 .

18
[ 6825-20-3 ]
[ 56525-79-2 ]

Yield	Reaction Conditions	Operation in experiment
33%		3.6-Diphenyl-9H-carbazole The same method as employed in the preparation of Intermediate 7 but starting from 3,6-dibromo-9H-carbazole gave after flash chromatography the title compound as a white solid in a 33percent yield. M.p.: 145-147 °C. 1H NMR (CDCl3, 300 MHz) delta 8.32 (d, 2H,J= 1.2 Hz), 8.09 (s, 1H), 7.72-7.66 (m, 6H), 7.50-7.43 (m, 6H), 7.35-7.30 (m, 2H).

References: [1]Patent: EP1094063,2001,A1 .

19
[ 625854-02-6 ]
[ 56525-79-2 ]
9-[4-(3,6-diphenyl-N-carbazolyl)] phenyl-10-phenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 110℃; for 10h;	Next, a synthetic method of DPCzPA by coupling reaction of 3, 6-diphenylcarbazole and 9-phenyl-10-(4-bromophenyl) anthracene will be shown. A mixture of 819 mg (2.0 mmol) of 9-phenyl-10-(4-bromophenyl) anthracene, 666 mg (2.1 mmol) of 3, 6-diphenylcarbazole, 14 mg (0.02 mmol) of dibenzylidine palladium (II), 1.0 g (10 mmol) of t-butoxy sodium, 0.1 mL of tri(t-butyl) phosphine, 20 mL of toluene is refluxed at 110 0C for 10 hours. After the reaction, the solution is rinsed with water, aqueous layer is extracted with toluene, and it is rinsed together with the organic layer using saturated salt solution, and thereafter dried with magnesium sulfate. An oily product obtained by natural filtration and condensation is dissolved in toluene, and filtered through celite, Florisil, and alumina. The filtrate is condensed, and purified by silica gel column chromatography (toluene). Recrystallization is carried out using dichloromethane and hexane to obtain 937 mg of DPCzPA at a yield of 71 percent. A synthetic scheme of DPCzPA by coupling reaction of 3, 6-diphenylcarbazole and 9-phenyl-10-(4-bromophenyl) anthracene is shown below.

References: [1]Patent: WO2006/104221,2006,A1 .Location in patent: Page/Page column 65.

20
[ 123291-15-6 ]
[ 56525-79-2 ]
C₇₁H₄₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		A solution was prepared by stirring tris(dibenzylideneacetone)dipalladium(0) chloroform complex (0.104 g), tri(t-butyl)phosphine (0.162 g), and toluene (5 ml) under nitrogen atmosphere at 60°C for 10 min. This solution was added to a mixture heated to 60°C of 2,6-bis(3-bromophenyl)-4-phenylpyridine (1.30 g), <strong>[56525-79-2]3,6-diphenylcarbazole</strong> (2.68 g), t-butoxysodium (1.18 g), and toluene (25 ml) under nitrogen atmosphere, and the resulting mixture was stirred at 110°C for 8 hr. The mixture was allowed to cool to room temperature and concentrated, and methanol was added thereto. The resulting precipitate was collected by filtration and washed with a water/methanol mixture solution. The precipitate was purified by silica-gel column chromatography (n-hexane/toluene = 1/1) and washed with an N,N-dimethylformamide/ethanol mixture solution and a methylene chloride/methanol mixture solution and then dried under reduced pressure to obtain a target compound 24 (1.81 g, yield: 69percent) as a white crystal. This white crystal was purified by sublimation to yield 1.35 g of a white solid. The white solid was confirmed to be a target compound 24 by DEI-MS (m/z = 924 (M+)). The compound had a vaporization temperature of 570°C and a glass transition temperature of 172°C. The melting point was not observed.

References: [1]Patent: EP1820801,2007,A1 .Location in patent: Page/Page column 89.

21
[ 56525-79-2 ]
[ 83-53-4 ]
[ 1068160-44-0 ]

Yield	Reaction Conditions	Operation in experiment
6%	With potassium phosphate; copper(l) iodide; In 1,4-dioxane; for 15h;Heating / reflux;	Preparation of 4'-naphthyl-<strong>[56525-79-2]3,6-diphenylcarbazole</strong> Reaction 6As depicted in Reaction 6, a solution of 1Og (31.3 mmol) of carbazole, 13.5g (31.3 mmol) of 1,4-dibromonaphthalene, CuI, diaminohexane and K3PO4 in dioxane was refluxed for 15 hours. After completion of the reaction, the reaction mixture was <n="32"/>extracted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was purified by column chromatography to give the title compound. The product was collected by filtration under reduced pressure and dried. Yield: 6percent. MS (El) (Calcd. for C34H22BrN: 523.09, Found: 523).

References: [1]Patent: WO2008/120899,2008,A1 .Location in patent: Page/Page column 29-30.

22
[ 56525-79-2 ]
[ 1224839-29-5 ]
[ 1224836-23-0 ]

Yield	Reaction Conditions	Operation in experiment
28%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; at 100℃; for 24h;Inert atmosphere;	b) 4.00 g of S-9 (12.5 mmol), 3.75 g of S-1 (5.69 mmol), 0.40 g (1.02 mmol) 2-of dicyclo- hexylphosphino-2'-(N,N-dimethylamino)biphenyl and 3.38 g (15.93 mmol) of potassium phosphate are stirred under argon in 47 ml toluene. 0.31 g (0.34 mmol) of tris(dibenzylidene- acetone) palladium(ll) are added and the reaction is stirred at 1000C for 24h. At room temperature, a 1 percent aqueous solution of NaCN is added to the medium which is boiled for 20 min. Ethyl acetate is added and the organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude product is purified by chromatography over silica gel (dichloromethane/cyclohexane 1 :1 ) and further purified by preparative HPLC to give 1.6 g of a white solid (28percent). 1H NMR (CDCI3, 300 MHz) 8.42 (m, 4H), 7.77-7.69 (m, 16H), 7.56-7.44 (m, 12H), 7.41-7.30 (m, 8H), 7.17-7.13 (m, 6H), 6.99-6.96 (m, 2H).

References: [1]Patent: WO2010/46259,2010,A1 .Location in patent: Page/Page column 55-56.

23
[ 6825-20-3 ]
phenylboronic acid, K₂CO₃ (2 mol), Pd(PPh₃)4 [ No CAS ]
[ 56525-79-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	In toluene;	Preparation of 3,6-diphenylcarbazole As depicted in Reaction 5, 15 g (46 mmol) of 3,6-dibromocarbazole, 14 g (92 mmol) of phenylboronic acid, K2CO3 (2 mol), Pd(PPh3)4 and toluene were refluxed for 10 hours. The reaction mixture was extracted with methylene chloride. The solvent was removed, and then the residue was purified by column chromatography (eluent:hexane) to give the title compound. Yield: 73percent. MS (EI) (Calcd. for C24H17N, 319.14. Found: 319).

References: [1]Patent: US2010/156283,2010,A1 .

24
[ 56525-79-2 ]
[ 354771-48-5 ]
[ 1333108-01-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In water; xylene; at 140℃; for 6h;Inert atmosphere;	Method of Synthesizing 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]-3-phenylquinoxaline (abbreviation: Cz1PQ-III)First, into a 200-mL three-neck flask were placed 2.2 g (6.0 mmol) of 2-(4-bromophenyl)-3-phenylquinoxaline, 1.9 g (6.0 mmol) of <strong>[56525-79-2]3,6-diphenyl-9H-carbazole</strong>, and 1.1 g (12.0 mmol) of sodium tert-butoxide.The air in the flask was replaced with nitrogen, and 60 mL of xylene was placed into this flask.The mixture was degassed by stirring under reduced pressure.To this mixture were added 0.2 mL of tri(tert-butyl)phosphine and 71 mg (0.12 mmol) of bis(benzylideneacetone)palladium(0).This mixture was stirred under a nitrogen stream at 140° C. for 6 hours.After the predetermined time had elapsed, water was added to the obtained mixture, and the mixture was separated into an organic layer and an aqueous layer.Organic substances were extracted with toluene from the aqueous layer.The solution of the obtained extract was combined with the organic layer, and the mixture was washed with saturated brine and dried with magnesium sulfate.The obtained mixture was gravity filtered, and the filtrate was concentrated to give an oily substance.This oily substance was purified by silica gel column chromatography (with a developing solvent of toluene), followed by recrystallization from toluene, whereby 3.0 g of a yellow powder of Cz1PQ-III, which is the substance to be produced, was obtained in 81percent yield.By a train sublimation method, 3.2 g of the obtained yellow powder of Cz1PQ-III, which is the substance to be produced, was sublimated and purified.In the sublimation and the purification, the yellow powder was heated at 300° C. under a pressure of 2.3 Pa with a flow rate of argon gas of 5 mL/min.After that, 3.1 g of a yellow powder of Cz1PQ-III, which is the substance to be produced, was obtained in 96percent yield.The synthesis scheme of Cz1PQ-III is illustrated in the following (a-3).Further, 1H NMR data of the obtained compound are as follows: 1H NMR (CDCl3, 300 MHz): delta=7.34-7.38 (m, 2H), 7.43-7.53 (m, 9H), 7.60-7.86 (m, 14H), 8.22-8.26 (m, 2H), 8.40 (d, J=1.5 Hz, 2H).

References: [1]Patent: US2011/245495,2011,A1 .Location in patent: Page/Page column 37-38.

25
[ 56525-79-2 ]
[ 3164-13-4 ]
[ 1215232-02-2 ]