[ CAS No. 170230-27-0 ] {[proInfo.proName]}

Name: 170230-27-0|(4-(Pyridin-2-yl)phenyl)boronic acid|98%
Brand: Ambeed
SKU: A134063
Price: 11.0 USD
Availability: InStock
Rating: 97 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 170230-27-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 170230-27-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 170230-27-0 ]

SDS Specification

Alternatived Products of [ 170230-27-0 ]

Product Details of [ 170230-27-0 ]

CAS No. :	170230-27-0	MDL No. :	MFCD17013972
Formula :	C₁₁H₁₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BANFGGCAQWUIAJ-UHFFFAOYSA-N
M.W :	199.01	Pubchem ID :	18980112
Synonyms :

Calculated chemistry of [ 170230-27-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	59.5
TPSA :	53.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.42
Log Po/w (WLOGP) :	0.43
Log Po/w (MLOGP) :	0.32
Log Po/w (SILICOS-IT) :	0.36
Consensus Log Po/w :	0.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.742 mg/ml ; 0.00373 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	1.42 mg/ml ; 0.00716 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0728 mg/ml ; 0.000366 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.03

Safety of [ 170230-27-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 170230-27-0 ]

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

Upstream synthesis route of [ 170230-27-0 ]
Downstream synthetic route of [ 170230-27-0 ]

[ 170230-27-0 ] Synthesis Path-Upstream 1~3

1
[ 63996-36-1 ]
[ 121-43-7 ]
[ 170230-27-0 ]

Yield	Reaction Conditions	Operation in experiment
65.8%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere Stage #2: at -78 - 20℃; for 16 h; Inert atmosphere	(2) Weigh 5.0 g (21.36 mmol) of compound 1 in a three-30 mL of anhydrous tetrahydrofuran (THF) was added by a syringe under a nitrogen atmosphere,The temperature of the system was lowered to -78 ° C using an acetone / liquid nitrogen bath,11.2 mL (2.5 M) of n-BuLi (n-BuLi) solution was slowly added dropwise with a syringe,The reaction was stirred at -78 ° C for 1 hour.Under nitrogen atmosphere, 7.4 mL (64.08 mmol)(B (OMe) 3),Remove the acetone / liquid nitrogen bath,The reaction was stirred at room temperature for 16 hours.Water quenching reaction,The mixture was extracted with dichloromethane (CH2Cl2)The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated.With petroleum ether precipitation, a white solid precipitation,The filter cake was filtered and vacuum dried,To give 2.80 g (yield 65.8percent) of a white solid,By NMR characterization,The product was the target product 2:

Reference： [1] Chemistry of Materials, 2016, vol. 28, # 23, p. 8556 - 8569
[2] Patent: CN105859793, 2016, A, . Location in patent: Paragraph 0029; 0030; 0032

2
[ 5467-74-3 ]
[ 170230-27-0 ]

Reference： [1] Chemistry of Materials, 2016, vol. 28, # 23, p. 8556 - 8569
[2] Patent: CN105859793, 2016, A,

3
[ 109-04-6 ]
[ 170230-27-0 ]

Reference： [1] Chemistry of Materials, 2016, vol. 28, # 23, p. 8556 - 8569
[2] Patent: CN105859793, 2016, A,

[ 170230-27-0 ] Synthesis Path-Downstream 1~88

1
[ 34837-55-3 ]
[ 170230-27-0 ]
[ 1235120-78-1 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4864 - 4867

2
[ 170230-27-0 ]
[ 1228585-13-4 ]
[ 1228585-24-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 19h;Inert atmosphere; Reflux;	In a stream of argon, 4- (2-pyridyl)phenylboronic acid (2.25 g), 2,4-bis(5-chlrobiphenyl-3-yl)-6-phenyl-1,3,5-triazine (2.00 g), cesium carbonate (3.68 g), palladium acetate (33.9 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (143 mg) were suspended in tetrahydrofuran (150 mL), and the suspension was refluxed for 19 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (1:100 - 1:75) mixed liquid as a developing solvent to give 2.47 g of the target 6-phenyl-2,4-bis[4-(2-pyridyl)-1,1':3',1'-terphenyl-5'-yl]-1,3,5-triazine as a white powder (yield: 85%). 1H-NMR(CDCl3) :delta7.26-7.30(m,2H),7.45(brt,J=7.3Hz,2H),7.53 -7.64(m,7H), 7.79-7.85(m,8H),7.93(d,J=8.4Hz,4H),8.12(t,J=1.7Hz, 2H),8.19(d,J=8.4Hz,4H),8.75(brd,J=5.0Hz,2H),8.84(brdd,J=7.5, 1.7Hz,2H),9.01(t,J=1.7Hz,2H),9.06(t,J=1.7Hz,2H). 13C-NMR(CDCl3) :delta120.6(CH2) ,122.3(CH2) ,126.6(CH2),126.9 (CH2),127.6(CH4),127.7(CH4),127.78(CH4),127.81(CH2),128.7 (CH2),129.0(CH4),129.1(CH2),130.1(CH2),132.7(CH),136.0 (quart.2),136.9(CH2),137.4(quart.),138.8(quart.2),140.8 (quart.2),141.2(quart.),141.4(quart.2),142.4(quart.2),149.8 (CH2),157.0(quart.2),171.76(quart.2),171.84(quart.).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 22

3
[ 170230-27-0 ]
[ 1228585-14-5 ]
[ 1228585-26-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 17h;Inert atmosphere; Reflux;	In a stream of argon, 4- (2-pyridyl)phenylboronic acid (2.47 g), 2,4-bis(5-chlro-4'-methylbiphenyl-3-yl)-6-phenyl-1,3,5-triazine (2.30 g), cesium carbonate (4.04 g), palladium acetate (37.0 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (157 mg) were suspended in tetrahydrofuran (200 mL), and the suspension was refluxed for 17 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (0:100 - 1:100) mixed liquid as a developing solvent to give 3.10 g of the target 6-phenyl-2,4-bis[4-(2-pyridyl)-4'-methyl-1,1':3',1'-terphenyl-5'-yl]-1,3,5 -triazine as a white powder (yield: 95%). 1H-NMR(CDCl3) :delta2.46(s,6H) ,7.24-7.30(m,2H) ,7.36(d,J= 8.OHz,4H),7.57-7.65(m,3H),7.72(d,J=8.OHz,4H),7.78-7.85(m,4H), 7.92(d,J=8.4Hz,4H) ,8.09(t,J=1.6Hz,2H) ,8.18(d,J=8.4Hz,4H) ,8.74 (brd,J=4.6Hz,2H) ,8.83 (brdd,J=7.6,1.6Hz,2H) ,8.99(t,J=1.6Hz,2H) , 9.02(t,J=1.6Hz,2H). 13C-NMR (CDCl3): delta21.3 (CH32 ) ,120.6 (CH2), 122.2 (CH2) ,126.4 (CH2),126.8(CH2),127.3(CH4),127.5(CH4),127.8(CH4),128.7 (CH2),129.1(CH2),129.7(CH4),130.0(CH2),132.7(CH),136.1 (quart.2),136.8(CH2),137.4(quart.2),137.6(quart.2),137.9 (quart.2),138.7(quart.),141.7(quart.2),141.8(quart.2),142.8 (quart.2),149.8(CH2),157.0(quart.2),171.82(quart.*2),171.84 (quart.).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 23

4
[ 170230-27-0 ]
[ 1228585-16-7 ]
[ 1228585-28-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 16h;Inert atmosphere; Reflux;	In a stream of argon, 4- (2-pyridyl)phenylboronic acid (1.21 g), 2,4-bis(5-chlrobiphenyl-3-yl)-6-p-tolyl-1,3,5-triazine (1.50 g), cesium carbonate (1.97 g), palladium acetate (24.7 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (105 mg) were suspended in tetrahydrofuran (135 mL), and the suspension was refluxed for 16 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a hexane/chloroform (2:3) mixed liquid as a developing solvent to give 1.85 g of the target 2,4-bis[4-(2-pyridyl)-1,1':3',1'-terphenyl-5'-yl]-6-p-tolyl-1,3,5 -triazine as a white powder (yield: 86%). 1H-NMR(CDCl3) :delta2.41(s,3H),7.16-7.22(m,2H) ,7.31(brd,J=8.1 Hz,2H),7.37(brt,J=7.3Hz,2H),7.47(brt,J=7.3Hz,4H),7.67-7.76(m, 8H) ,7.83(d,J=8.4Hz,4H) ,8.00(t,J=1.6Hz,2H) ,8.09(d,J=8.4Hz,4H) , 8.62(d,J=8.2Hz,2H),8.67(brddd,J=4.6,1.3,1.3Hz,2H),8.91(t,J=1.6 Hz, 2H),8.94(t,J=1.6Hz, 2H). 13C-NMR (CDCl3) : delta21.8 (CH3), 120.5 (CH2), 122.2 (CH2), 126.6 (CH2),126.9(CH2),127.45(CH4),127.47(CH4),127.7(CH4),127.8 (CH2),129.0(CH4),129.1(CH2),129.5(CH2),130.0(CH2),133.5 (quart.),136.8(CH2),137.6(quart.2),138.8(quart.2),140.9 (quart.2),141.4(quart.2),141.7(quart.2),142.4(quart.2), 143.4(quart.),149.8(CH2),157.1(quart.2),171.7(quart.2), 171.9(quart.).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 24

5
[ 170230-27-0 ]
[ 1228585-17-8 ]
[ 1228585-30-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 22h;Inert atmosphere; Reflux;	In a stream of argon, <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (2.06 g), 2,4-bis(5-chlrobiphenyl-3-yl)-6-(2-naphthyl)-1,3,5-triazine (2.00 g), cesium carbonate (3.68 g), palladium acetate (31.0 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (132 mg) were suspended in tetrahydrofuran (150 mL), and the suspension was refluxed for 22 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (0:100 -1:66) mixed liquid as a developing solvent to give 2.67 g of the target 2-(2-naphthyl)-4,6-bis[4-(2-pyridyl)-1,1':3',1'-terphenyl-5'-yl]-1,3,5-triazine as a white powder (yield: 95%). 1H-NMR(CDCl3) :delta7.26-7.33(m,2H),7.49(brt,J=7.3Hz,2H) ,7.56 -7.67(m,6H),7.80-7.87(m,8H),7.94-7.97(m,1H),7.95(d,J=8.4Hz,4H) ,8.05(d,J=8.7Hz,1H),8.12(t,J=1.6Hz,2H),8.12-8.14(m,1H),8.23(d, J=8.4Hz,4H),8.78(brddd,J=4.6,1.3,1.3Hz,2H),8.87(dd,J=8.7,1.6 Hz,1H),9.06(t,J=1.6Hz,2H),9.10(t,J=1.6Hz,2H),9.34(brs,1H). 13C-NMR(CDCl3) : delta120. 5 (CH2) ,122.2 (CH2),125.2(CH) ,126.4 (CH),126.6(CH2),126.9(CH2),127.5(CH8),127.7(CH4),127.77(CH 2),127.84(CH),127.9(CH),128.4(CH),129.0(CH4),129.7(CH),130.0 (CH2),130.2(CH),133.1(quart.),133.5(quart.),135.8(quart.), 136.8(CH2),137.4(quart.2),138.8(quart.2),140.8(quart.2), 141.3(quart.2),141.6(quart.2),142.4(quart.2),149.8(CH2), 157.0(quart.2),171.7(quart.*2),171.9(quart.).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 25; 26

6
[ 170230-27-0 ]
[ 1228585-18-9 ]
[ 1228585-29-2 ]

Yield	Reaction Conditions	Operation in experiment
49%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 19h;Inert atmosphere; Reflux;	In a stream of argon, 4- (2-pyridyl) phenylboronic acid (1.19 g), 2,4-bis(5-chlrobiphenyl-3-yl)-6-(1,1':3',1'-terphenyl-5'-yl)-1,3,5-triazine (1.36 g), cesium carbonate (1.95 g), palladium acetate (17.9 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (75.9 mg) were suspended in tetrahydrofuran (160 mL), and the suspension was refluxed for 19 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (0:100 - 1:66) mixed liquid as a developing solvent to give 890 mg of the target 2,4--bis[4-(2-pyridyl)-1,1':3',1'-terphenyl-5'-yl]-6-(1,1':3',1'-terphenyl-5'-yl)-1,3,5-triazine as a white powder (yield: 49%). 1H-NMR(CDCl3):delta7.27-7.32 (M,2H) 7.44-7.50(m,4H) 7.53-7.60 (m,8H),7.78-7.87(m,12H) ,7.94(d,J=8.4Hz,4H) ,8.09(t,J=1.7Hz,1H) , 8.14(t,J=1.7Hz,2H) ,8.19(d,J=8.4Hz,4H) ,8.78(brddd,J=4.6,1.3,1.3 Hz,2H) ,9.03(d,J=1.7Hz,2H) ,9.05(t,J=1.7Hz,2H) ,9.08(t,J=1.7Hz, 2H).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 24; 25

7
[ 170230-27-0 ]
[ 1228585-15-6 ]
[ 1228585-27-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 17h;Inert atmosphere; Reflux;	In a stream of argon, <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (116 mg), 2,4-bis(5-chlro-1,1':4':1'-terphenyl-3-yl)-6-phenyl-1,3,5-triazine (100 mg), cesium carbonate (190 mg), palladium acetate (3.3 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (14 mg) were suspended in tetrahydrofuran (15 mL), and the suspension was refluxed for 17 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (0:100 - 1:100) mixed liquid as a developing solvent to give 125 mg of the target 6-phenyl-2,4-bis[4-(2-pyridyl)-1,1':3',1':4'1''-quaterphenyl-5'-yl]-1,3,5-triazine as a white powder (yield: 93%). 1H-NMR(CDCl3):delta7.19-7.22 (m,2H) 7.29-7.35 (m,2H) 7.42 (brt, J=7.3Hz,4H),7.55-7.65(m,7H),7.71-7.79(m,8H),7.85(d,J=7.3Hz, 4H),7.88(d,J=8.4Hz,4H),8.10(t,J=1.8Hz,2H),8.13(d,J=8.4Hz,4H), 8.68(brd,J=4.7Hz,2H),8.78(brd,J=7.9Hz,2H),9.01(d,J=1.7Hz,4H).

Reference： [1]Patent: EP2361909,2011,A1 .Location in patent: Page/Page column 23; 24

8
[ 170230-27-0 ]
[ 1318242-09-9 ]
[ 1318241-98-3 ]

Reference： [1]Organometallics,2011,vol. 30,p. 4453 - 4458

9
[ 170230-27-0 ]
[ 1268250-63-0 ]
[ 1268250-64-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With caesium carbonate; XPhos;palladium diacetate; In tetrahydrofuran; for 18h;Inert atmosphere; Reflux;	In a stream of argon, 1.14 g (2.15 mmol) of 4,6-bis(2-biphenylyl)-2-(3,5-dichlorophenyl)pyrimidine, 0.90 g (4.52 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong>, 1.47 g (4.52 mmol) of cesium carbonate, 19 mg (0.086 mmol) of palladium acetate and 82 mg (0.172 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were suspended in 40 mL of tetrahydrofuran, and the obtained suspension was heated under reflux for 18 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. The thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:1) mixed solvent as an eluent to give 0.60 g of the target 4,6-bis(2-biphenylyl) -2- [4,4"-di(2-pyridyl) -1,1' :3' ,1"--terphenyl-5'-yl]pyrimidine as a white solid (yield: 37%). 1H-NMR(CDCl3):delta7.04(s,1H),7.22-7.36(m,10H),7.45-7.59(m,8H), 7.80-7.89(m,8H),7.96(t,J=1.8Hz,1H),8.18(d,J=8.3Hz,4H),8.25(d,J= 1.8Hz,2H),8.78(bd,J=4.8Hz,2H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 36-37

10
[ 170230-27-0 ]
[ 1268250-65-2 ]
[ 1268250-66-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With caesium carbonate; XPhos;palladium diacetate; In tetrahydrofuran; for 17h;Inert atmosphere; Reflux;	In a stream of argon, 0.50 g (1.32 mmol) of 2-(3,5-dichlorophenyl)-4,6-di(2-pyridyl)pyrimidine, 0.55 g (2.76 mmol) of 4- (2-pyridyl)phenylboronic acid, 0. 90 g (2.77 mmol) of cesium carbonate, 24 mg (0.106 mmol) of palladium acetate and 101 mg (0.211 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were suspended in 30 mL of tetrahydrofuran, and the obtained suspension was heated under reflux for 17 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate and the thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using chloroform as an eluent to give 0.46 g of the target 2-[4,4"-di(2-pyridyl)-1,1' :3',1"-terphenyl-5'-yl]-4,6-di(2-pyridyl)pyrimidine as a white solid (yield: 56%). 1H-NMR(CDCl3):delta7.17-7.26(m,2H),7.40(ddd,J=7.5,4.8,1.0Hz,2H), 7.69-7.78(m,4H),7.83-7.89(m,6H),8.00(t,J=1.6Hz,1H),8.12(d,J=8.3 Hz,4H),8.67-8.70(m,4H),8.74(d,J=4.0Hz,2H),8.94(d,J=1.8Hz,2H),9.31 (s,1H). 13C-NMR(CDCl3):delta112.0(CH),120.6(CH×2,CH×2),122.0(CH×2),122. 3(CH×2),125.4(CH×2),126.5(CH×4),127.5(CH×4),127.9(CH),136.9(CH×2) ,137.1(CH×2),138.7(quart.×2),139.2(quart.),141.7(quart.×2), 141.8(quart.×2),149.7(CH×2),149.8(CH×2),154.7(quart.×2), 157.1 (quart.×2),163.9(quart.),164.5(quart.×2).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 37

11
[ 170230-27-0 ]
[ 1268250-99-2 ]
[ 1268250-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 70℃; for 12h;Inert atmosphere;	In a stream of argon, 1.91 g (8.56 mmol) of 9-phenanthreneboronic acid, 4.00 g (8.56 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 98.9 mg (0.086 mmol) of tetrakis (triphenylphosphine) palladium were suspended in a mixed solvent composed of 320 mL of toluene and 40 mL of ethanol, and the resultant suspension was heated to 60C. To the suspension, 25.7 mL (25.7 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 4 hours. Then the mixture was cooled to room temperature, and 2.56 g (12.8 mmol) of 4- (2-pyridyl)phenylboronic acid and 25.7 mL (25.7 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 70C and maintained at that temperature for 12 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 3.91 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4'-(2-pyridyl) biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 64%) . 1H-NMR(CDCl3):delta.7.31(d,J=7.00Hz,1H),7.58-7.65(m,8H),7.70(t, J=7.0Hz,1H),7.76(t,J=7.0Hz,2H),7.82-7.87(m,2H),7.93(s,1H),7.99(d, J=8.5Hz,2H),8.02(d,J=8.2Hz,1H),8.06(d,J=8.0Hz,1H),8.12(s,1H),8.23 (d,J=8.4Hz,2H),8.78(d,J=8.2Hz,1H),8.82(d,J=8.1Hz,4H),8.89(d,J=8.2 Hz,1H),8.98(s,1H),9.21(s,1H). The obtained triazine compound exhibited a Tg of 133C.

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 43

12
[ 170230-27-0 ]
[ 1380444-38-1 ]
[ 1268250-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 17h;Inert atmosphere;	In a stream of argon, 0.98 g (3.21 mmol) of 9-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)anthracene, 1.50 g (3.21 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 37.1 mg (0.032 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 100 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 60C. To the suspension, 9.63 mL (9.63 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0. 96 g (4.82 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> and 6.42 mL (6.42 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60C and maintained at that temperature for 17 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.68 g of the target 2- [5- (9-anthryl) -4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 33%). 1H-NMR(CDCl3):delta.7.34(brs,1H),7.44(t,J=7.6Hz,2H),7.53-7.64 (m,9H),7.85-7.88(m,4H),8.01(d,J=7.6Hz,2H),8.03(s,1H),8.16(d,J=8.5 Hz,2H)8.23(d,J=8.3Hz,2H),8.64(s,1H),8.79(d,J=5.6Hz,4H),8.89(s, 1H),9.31(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 44

13
[ 170230-27-0 ]
[ 1380444-39-2 ]
[ 1268250-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 70℃; for 3h;Inert atmosphere;	In a stream of argon, 0.37 g (2.14 mmol) of 1-naphthaleneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 24.7 mg (0.021 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 80 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 60C. To the suspension, 8.56 mL (8.56 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.64 g (3.21 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> wad added. Then the mixture was heated to 70C and maintained at that temperature for 3 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.61 g of the target 4,6-diphenyl-2-[5-(1-naphthyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 49%). 1H-NMR(CDCl3):delta.7.32(t,J=6.5Hz,1H),7.53(t,J=6.9Hz,1H),7.57-7.68(m,10H),7.83-7.87(m,2H),7.98(d,J=8.4Hz,2H),8.00-8.05(m,2H), 8.07(s,1H),8.23(d,J=6.7Hz,2H),7.79(d,J=6.5Hz,1H),8.82(d,J=8.5Hz, 4H),8.93(s,1H),9.18(s,1H). The obtained triazine compound exhibited a Tg of 107C.

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 45

14
[ 170230-27-0 ]
C₃₇H₂₂BrN₃ [ No CAS ]
4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 70℃; for 3h;Inert atmosphere;	In a stream of argon, 0.53 g (2.14 mmol) of 1-pyreneboronic acid, 1.00 g (2.14 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 24.7 mg (0.0214 mmol) of tetrakis(triphenylphosphine)palladium were-suspended in a mixed solvent composed of 80 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 60C. To the suspension, 8.56 mL (8.56 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.64 g (3.21 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> wad added. Then the mixture was heated to 70C and maintained at that temperature for 3 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.37 g of the target 4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 26%). 1H-NMR(CDCl3):delta.7.35(brs,1H),7.57-7.65(m,6H),7.86-7.91(m, 2H),8.03(d,J=8.4Hz,2H),8.08(t,J=7.6Hz,1H),8.13(d,J=9.3Hz,1H),8.18 -8.29(m,8H),8.33(d,J=9.3Hz,1H),8.37(d,J=7.8Hz,1H),8.80(d,J=4.8Hz, 1H),8.83(d,J=7.9Hz,4H),9.07(s,1H),9.23(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 46

15
[ 170230-27-0 ]
C₄₇H₃₀BrN₃ [ No CAS ]
[ 1268250-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 4h;Inert atmosphere;	In a stream of argon, 0.54 g (2.42 mmol) of 9-phenanthreneboronic acid, 1.50 g (2.42 mmol) of 4,6-bis(biphenyl-3-yl)- 2-(3,5-dibromophenyl)-1,3,5-triazine and 56.0 mg (0.048 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 150 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 60C. To the suspension, 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.72 g (3.63 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> and 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60C and maintained at that temperature for 4 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 1.1 g of the target 4,6-bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 58%). 1H-NMR(CDCl3):delta.7.34(brs,1H),7.43(t,J=7.4Hz,2H),7.52(t,J= 7.4Hz,4H),7.66(t,J=8.1Hz,1H),7.68(t,J=7.7Hz,2H),7.70(t,J=7.7Hz, 1H),7.74-7.78(m,2H),7.76(d,J=8.4Hz,4H),7.87(d,J=7.6Hz,4H),7.94(s, 1H),8.00(d,J=8.4Hz,2H),8.01(d,J=7.7Hz,1H),8.12(t,J=7.4Hz,1H),8.14 (s,1H),8.23(d,J=8.3Hz,2H),8.80(d,J=7.8Hz,1H),8.80(d,J=7.8Hz,2H), 8.82(d,J=8.3Hz,1H),8.88(d,J=8.3Hz,1H),9.01(s,1H),9.05(s,2H),9.21 (s,1H). The obtained triazine compound exhibited a Tg of 119C

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 47

16
[ 170230-27-0 ]
[ 1380445-02-2 ]
[ 1268250-90-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 4h;Inert atmosphere;	In a stream of argon, 0.714 g (3.22 mmol) of 9-phenanthreneboronic acid, 1.50 g (3.22 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine and 37.2 mg (0.0322 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 120 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 9.66 mL (9.66 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. Then the mixture was cooled to room temperature, and 0.961 g (4.83 mmol) of 4- (2-pyridyl)phenylboronic acid and 9.66 mL (9.66 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60C and maintained at that temperature for 4 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added-to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 1.28 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4'-(2-pyridyl)biphenyl-3-yl]-pyrimidine as a white solid (yield: 62%). 1H-NMR(CDCl3):delta. 7.25(t,J=4.9Hz,1H),7.53-7.58(m,6H),7.60 (d,J=7.5Hz,1H),7.66(t,J=7.0Hz,1H),7.12(t,J=8.2Hz,2H),7.62-7.83(m, 2H),7.90(s,1H),7.95-8.00(m,4H),8.07(d,J=8.1Hz,1H),8.09(s,1H),8.17 (d,J=8.5Hz,1H),8.30-8.32(m,4H),8.73(d,J=5.0Hz,1H),8.79(d,J=8.3Hz, 1H),8.84(d,J=8.2Hz,1H),8.90(s,1H),9.14(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 51

17
[ 170230-27-0 ]
[ 1268250-60-7 ]
[ 1268250-61-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate; XPhos;palladium diacetate; In 1,4-dioxane; for 17h;Inert atmosphere; Reflux;	In a stream of argon, 1.50 g (3.98 mmol) of 2-(3,5-dichlorophenyl)-4,6-diphenylpyrimidine, 1.74 g (8.75 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong>, 2.85 g (8.75 mmol) of cesium carbonate, 36 mg (0.159 mmol) of palladium acetate and 152 mg (0.318 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were suspended in 80 mL of 1,4-dioxane, and the obtained suspension was heated under reflux for 17 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate and the thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using chloroform as an eluent to give 2.19 g of the target 2-[4,4"-di(2-pyridyl)-1,1' :3',1"-terphenyl-5'-yl]-4,6-diphenylpyrimidine as a white solid (yield: 90%). 1H-NMR(CDCl3):delta7.19-7.23(m,2H),7.53-7.50(m,6H),7.70-7.79(m, 4H),7.88(d,J=8.5Hz,4H),8.01-8.02(m,2H),8.11(d,J=8.3Hz,4H),8.25-8.29(m,4H),8.68(d,J=4.5Hz,2H),8.95(d,J=1.8Hz,2H). 13C-NMR(CDCl3):delta110.7(CH),120.5(CH×2),122.2(CH×2),126.6 (CH×2),127.4(CH×4),127.5(CH×4),127.9(CH×4),128.2(CH),129.0(CH×4), 130.9(CH×2),136.8(CH×2),137.5(quart.×2),138.7(quart.×2),139.5 (quart.),141.6(quart.),141.8(quart.),149.9(CHx2),157.1(quart.), 164.4(CH),165.0(CHx2).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 35

18
[ 170230-27-0 ]
C₃₅H₂₂BrN₃ [ No CAS ]
4,6-diphenyl-2-[5-(2-phenanthryl)-4'-(2-pyrimidyl)biphenyl-3-yl]-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 17h;Inert atmosphere;	In a stream of argon, 77.6 mg (0.167 mmol) of 2-phenanthreneboronic acid, 37 mg (0.167 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 5.78 mg (0.0050 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 7 mL of toluene and 0.8 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 0.50 mL (0.50 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 2 hours. The resultant reaction mixture was cooled to room temperature, and then, 49.8 mg (0.25 mmol) of 4- (2-pyridyl)phenylboronic acid and 0.50 mL (0.50 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60C, and maintained at that temperature for 17 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 30 mg of the target 4,6-diphenyl-2-[5-(2-phenanthryl)-4'-(2-pyrimidyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 28%). 1H-NMR(CDCl3):delta.7.26-7.30(m,1H),7.52-7.66(m,7H),7.69-7.72 (m,1H),7.77-7.85(m,3H),7.89(d,J=8.9Hz,1H),7.95(t,J=7.1Hz,1H),7.96 (d,J=8.5Hz,2H),8.11(d,J=8.5Hz,2H),8.20(d,J=8.6Hz,2H),8.24(s,1H), 8.29(s,1H),8.74-8.76(m,2H),8.81(d,J=Hz,2H),8.82(d,J=Hz,2H),8.84 (d,J=8.8Hz,1H),9.06(s,1H),9.12(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 54

19
[ 170230-27-0 ]
[ 1380445-64-6 ]
[ 1268250-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 2h;Inert atmosphere;	In a stream of argon, 0.95 g (4 mmol) of 9,9-dimethyl-2-fluoreneboronic acid, 1.87 g (4 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 46.2 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 150 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 12 mL (12 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. The resultant reaction mixture was cooled to room temperature, and then, 1.19 g (6 mmol) of 4- (2-pyridyl)phenylboronic acid and 12 mL (12 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60C, and maintained at that temperature for 2 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 1.61 g of the target 2-[5-(9,9-dimethylfluoren-2-yl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 61.5%). 1H-NMR(CDCl3):delta.1.63(s,6H),7.31(dd,J=7.0,4.8,1H),7.38-7.44 (m,2H),7.52(d,J=6.5,H),7.60-7.68(m,6H),7.81-7.88(m,5H),7.93(d,J= 7.8,1H),7.98(d,J=8.5,2H),8.17(s,H),8.23(d,J=8.5,2H),8.78(d,J=4.8, 1H),8.85(d,J=8.1,4H),9.07(s,2H). The obtained triazine derivative exhibited a Tg of 118C.

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 56

20
[ 170230-27-0 ]
[ 1380445-81-7 ]
[ 1268250-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 3.5h;Inert atmosphere;	In a stream of argon, 0.71 g (3 mmol) of 9,9-dimethyl-2-fluoreneboronic acid, 1.4 g (3 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine and 34.7 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 115 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 9 mL (9 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. The resultant reaction mixture was cooled to room temperature, and then, 0.896 g (4.5 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> and 9 mL (9 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60C, and maintained at that temperature for 3.5 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.85 g of the target 2-[5-(9,9-dimethylfluoren-2-yl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenylpyrimidine as a white solid (yield: 43.3%). 1H-NMR(CDCl3):delta.1.63(s,6H)7.30(d,J=5.7Hz,1H)7.34-7.42(m, 2H),7.52(d,J=6.6Hz,1H),7.59-7.64(m,6H),7.82-7.92(m,6H),7.98(d,J= 8.4Hz,2H),8.10(d,J=6.8Hz,2H),8.21(d,J=8.4Hz,2H),8.37(d,J=6.3Hz, 4H),8.78(d,J=4.8Hz,1H),9.04(s,2H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 57

21
[ 170230-27-0 ]
[ 1380445-99-7 ]
[ 1268250-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 80℃; for 24h;Inert atmosphere;	In a stream of argon, 185 mg (0.644 mmol) of 9,9-dimethyl--2-benzo(c)fluoreneboronic acid, 300 mg (0.644 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 7.44 mg (0.00644 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 24 mL of toluene and 3 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 1.93 mL (1.93 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. The resultant reaction mixture was heated to 80C and further stirred for 3 hours. The reaction mixture was cooled to room temperature, and then, 256 mg (1.29 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> and 2.90 mL (2.90 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 80C, and maintained at that temperature for 24 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 172 mg of the target 2-[5-(9,9-dimethylbenzo(c)fluoren-2-yl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 38.0%). 1H-NMR(CDCl3):delta.1.63(s,6H),7.25-7.29(m,1H),7.42(t,J=7.4Hz, 1H),7.49-7.64(m,9H),7.69-7.73(m,1H),7.74(s,1H),7.79(t,J=8.1Hz, 1H),7.83(d,J=7.7Hz,1H),7.97(d,J=8.7Hz,2H),8.08(s,1H),8.11(d,J=7.8 Hz,1H),8.20(d,J=8.6Hz,2H),8.43(d,J=7.8Hz,1H),8.75(d,J=4.9Hz,1H), 8.79(d,J=8.3Hz,2H),8.80(d,J=8.1Hz,2H),8.91(d,J=8.5Hz,1H),8.94(s, 1H),9.18(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 58

22
[ 170230-27-0 ]
[ 1380446-19-4 ]
[ 1268250-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 60℃; for 15h;Inert atmosphere;	In a stream of argon, 0.538 g (2.42 mmol) of 9-phenanthreneboronic acid, 1.20 g (2.42 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine and 28.0 mg (0.0242 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 90 mL of toluene and 10 mL of ethanol, and the resultant suspension was heated to 50C. To the suspension, 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. The resultant reaction mixture was cooled to room temperature, and then, 0.722 g (3.63 mmol) of <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> and 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60C, and maintained at that temperature for 15 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.680 g of the target 4,6-di-p-tolyl-2-[5-(9-phenanthryl)-4'-(2-pyridyl) biphenyl-3-yl] -1,3,5-triazine as a white solid (yield: 42%). 1H-NMR(CDCl3):delta.2.47(s,6H),7.25-7.28(m,1H),7.35(d,J=8.0Hz, 4H),7.60(t,J=7.7Hz,1H),7.67(t,J=7.4Hz,1H),7.73(t,J=7.4Hz,1H),7.73 (t,J=7.4Hz,1H),7.79(t,J=7.8Hz,1H),7.83(d,J=7.8Hz,1H),7.90(s,1H), 7.95(d,J=8.4Hz,2H),7.98(d,J=8.0Hz,1H),8.04(d,J=7.9Hz,1H),8.07(s, 1H),8.18(d,J=8.5Hz,2H),8.66(d,J=8.1Hz,4H),8.74(d,J=5.0Hz,1H),8.79 (d,J=8.4Hz,1H),8.85(d,J=8.0Hz,1H),8.92(s,1H),9.16(s,1H).

Reference： [1]Patent: EP2468731,2012,A1 .Location in patent: Page/Page column 59

23
[ 636-28-2 ]
[ 170230-27-0 ]
[ 1334590-09-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium phosphate; palladium diacetate; XPhos; In water; toluene; for 44h;Inert atmosphere; Reflux;	Synthesis of Compound (1) [0067] [0068] In a stream of argon, 1.00 g (2.5 mmol) of 1,2,4,5-tetrabromobenzene, 4.04 g (20 mmol) of 4-(2-pyridyl)phenylboricacid, 28.5 mg (0.13 mmol) of palladium acetate, 121 mg (0.25 mmol) of 2-dicyclohexylphosphino--2',4',6'-triisopropylbiphenyl, and 5.39 g (25 mmol) of tripotassium phosphate were dissolved in a mixed solvent comprised of 10 mL of toluene and 1 mL of water. The obtained solution was heated under reflux for 44 hours. The reaction mixture was cooled to room temperature, and then, diluted with methanol and the solid was filtered. The thus-obtained crude product was purified by silica gel chromatography using a mixed solvent comprised of chloroform and hexane (2:1-1:0) as a developing solvent to give 1.38 g of the target 4,4"-di(2-pyridyl)-4',5'-bis[4-(2-pyridyl)phenyl]-1,1':2',1"-terphenyl as a white solid (yield: 79%). [0069] 1H-NMR (CDCl3) : delta7.21-7.53 (m, 4H), 7.44 (d, J=8. 44Hz-, 8H), 7.69(s,2H),7.53-7.79(m,8H),7.94(d,J=8.48Hz,8H),8.70(d,J= 4.56Hz,4H)

Reference： [1]Patent: EP2551264,2013,A1 .Location in patent: Paragraph 0067; 0068; 0069

24
[ 170230-27-0 ]
2-(3,5-dibromophenyl)-4-phenylquinazoline [ No CAS ]
4-phenyl-2-[4,4''-bis(2-pyridyl)-1,1':3',1''-terphenyl-5'-yl]quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; potassium carbonate; XPhos; In 1,4-dioxane; water; at 80℃;Inert atmosphere;	Under an argon atmosphere, 2-(3,5-dibromophenyl)-4-phenylquinazoline 742mg (1.69mmol), 4-(2-pyridyl)phenyl boronic acid 738mg (3.71mmol), palladium acetate 7.6mg (0 .0337mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl 32mg of (0.0674mmol) was added in dioxane 56 mL, was added further 3M- aqueous potassium carbonate 3.4 mL, It was heated and stirred overnight at 80C.After cooling to room temperature,filtered off solid precipitated by adding water, washed with water, methanol, and hexane. The resulting solid was recrystallizedfrom toluene, 4-phenyl-2-[4,4''-bis(2-pyridyl)-1,1':3',1''-terphenyl-5'-yl]quinazoline as a white solid (yield649 mg, 65% yield).

Reference： [1]Patent: JP2016/20332,2016,A .Location in patent: Paragraph 0163

25
[ 170230-27-0 ]
2-(3,5-dibromophenyl)-6-chloro-4-phenylquinazoline [ No CAS ]
6-chloro-4-phenyl-2-[4,4''-bis(2-pyridyl)-1,1':3',1''-terphenyl-5'-yl]quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Inert atmosphere; Reflux;	Under an argon atmosphere, 2-(3,5-dibromophenyl)-6-chloro-4-phenylquinazoline 1.91g (4.02mmol), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> 1.76g (8.84mmol) , and addition of tetrakis(triphenylphosphine)palladium 92.9mg (0.0804mmol) in THF 80mL, further 3M- added potassium carbonate aqueous solution 5.4mL, was heated to reflux overnight. After cooling to room temperature, filtered off solid precipitated by adding water, washed with water, methanol, and hexane. The resulting crude product was purified by silica gel column chromatography (developing solvent: chloroform), to give 6-chloro-4-phenyl-2-[4,4''-bis (2-pyridyl) -1,1':3',1''-terphenyl-5'-yl]quinazoline (A-1) to give a white solid (yield 1.41g, 56% yield).

Reference： [1]Patent: JP2016/20332,2016,A .Location in patent: Paragraph 0167

26
[ 170230-27-0 ]
5-bromo-benzo[b]pyrido[3',2':4,5]pyrrolo[1,2-f]phenanthridine [ No CAS ]
C₃₄H₂₁N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	5-bromo-benzo[b]pyrrolo[3',2':4,5]pyrrol[1,2-f]phenanthridine 2g (5.03 mmol), <strong>[170230-27-0](4-(pyridin-2-yl)phenyl)boronic acid</strong> (R4-B(OH)2), 1.20g (6.04 mmol), tetrakis(triphenylphosphine)palladium, 0.58g (0.50 mmol), potassium carbonate 2.09g (15.09 mmol) of toluene, H2O, ethanol mixed solution was stirred for 24 hours under reflux. When the reaction was completed, the reaction mixture extracted with EA, and the organic layer was dried over MgSO4. To a MC / Hex eluant separated by column chromatography to obtain the objective compound 107 1.97g (83%).

Reference： [1]Patent: KR2015/27659,2015,A .Location in patent: Paragraph 0100-0101; 0108-0109

27
[ 170230-27-0 ]
2-[3-chloro-5-(9-phenanthryl)phenyl]-4-phenyl-[1]benzofuro[ 3,2-d]pyrimidine [ No CAS ]
2-[5-(9-phenanthryl)-4'-(2-pyridyl)biphenyl-3-yl]-4-phenyl-[1]benzofuro[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; for 19h;Inert atmosphere; Reflux;	Under argon stream, compound B-7 (1.17g), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (482 mg), palladium acetate (9.9 mg), and in addition of 2-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (62.9 g) in THF (22mL), further 3M aqueous potassium carbonate solution (1.6 mL) was added, then heated to reflux for 19 hours. After cooling the reaction mixture to room temperature, water was added. The precipitated solid was washed with water, washed with methanol, by further washing with hexane, to give a gray solid. The resulting gray solid was dissolved in toluene, after filtering off the insoluble component, to precipitate a white solid by addition of methanol to the filtrate. By filtering off the precipitated solid, the desired 2-[5-(9-phenanthryl)-4'-(2-pyridyl)biphenyl-3-yl]-4-phenyl-[1]Benzofuro[3,2-d]pyrimidine (C-3) to obtain as grey powder (yield 1.24g, 87% yield).

Reference： [1]Patent: JP2015/205831,2015,A .Location in patent: Paragraph 0152-0153

28
[ 170230-27-0 ]
2-(3-bromo-5-chlorophenyl)-4-chloro-[1]benzofuro[3,2-d]pyrimidine [ No CAS ]
2-[4,4''-bis(2-pyridyl)-[1,1':3',1'']-terphenyl-5'-yl]-4-[4-(2-pyridyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; for 72h;Inert atmosphere; Reflux;	Under argon stream, compound B-2 (380mg), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (634 mg), palladium acetate (4.3 mg), and in addition of 2-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (18.3 mg) in THF (19mL), further 3M aqueous potassium carbonate solution (2.1 mL) was added , then heated to reflux for 72 hours. After cooling the reaction mixture to room temperature, water was added. The precipitated solid was washed with water, washed with methanol, by further washing with hexane, the desired 2-[4,4''-bis(2-pyridyl)-[1,1':3',1'']-terphenyl-5'-yl]-4-[4-(2-pyridyl)phenyl]-[1]Benzofuro[3,2-d]pyrimidine (C-2), as grey powder (yield 547mg 81% yield).

Reference： [1]Patent: JP2015/205831,2015,A .Location in patent: Paragraph 0146

29
[ 170230-27-0 ]
2-(3-bromo-5-chlorophenyl)-4-phenyl-[1]benzofuro[3,2-d]pyrimidine [ No CAS ]
2-[4,4''-bis(2-pyridyl)-[1,1':3',1'']terphenyl-5'-yl]-4-phenyl-[1]benzofuro[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; water; for 20h;Inert atmosphere; Reflux;	Under argon stream, compound B-3 (71mg), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (71 mg), palladium acetate (1.8 mg), and in addition to the 2-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (7.8mg) and THF (3.3mL), further 3M aqueous potassium carbonate solution (0.25mL) was added, then heated to reflux for 20 hours. After cooling the reaction mixture to room temperature, water was added. The precipitated solid was washed with water, washed with methanol, by further washing with hexane, the desired 2-[4,4''-bis(2-pyridyl)-[1,1':3',1'']-terphenyl-5'-yl]-4-phenyl-[1]Benzofuro[3,2-d]pyrimidine (C-1) as grey powder (yield 100 mg, 98% yield).

Reference： [1]Patent: JP2015/205831,2015,A .Location in patent: Paragraph 0143-0144

30
[ 1073062-42-6 ]
[ 170230-27-0 ]
4,6-diphenyl-2-{4-(2-pyridyl)-4'-[2-(4,6-dimethylpyrimidyl)]-1,1':3',1"-terphenyl-5'-yl}-1,3,5-triazine [ No CAS ]

Reference： [1]Patent: JP2015/27986,2015,A

31
[ 1073062-42-6 ]
[ 170230-27-0 ]
[ 1073062-46-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; for 16h;Inert atmosphere; Reflux;	Under an argon atmosphere, 2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (8.46g, 20.mmol), 4- (2- pyridyl) phenyl boronic acid ( 4.38 g, 22 mmol), tetrakis (triphenylphosphine) palladium (462.3mg, 0.40mmol), and sodium hydroxide (2.40 g, weighed 60.mmol), tetrahydrofuran (100 mL) and water (15 mL) It was suspended in. The mixture was heated to reflux for 16 hours. After cooling, water (150 mL) was added, and the precipitated solid was filtered off and washed with water, methanol, a solid with hexane. Further Purification by recrystallization (toluene) 2- [5-chloro-4 '- (2-pyridyl) dimethyl biphenyl-3-yl] -4,6-diphenyl-1,3,5-triazine as a white solid (yield 9.30g, 94% yield).
91%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 3h;Reflux;	Intermediate 1-A (50 g, 118.3 mmol), (4 - (pyridin-2-yl) phenyl) boronic acid (23.5 g, 118.3 mmol), K2CO3 (49.1 g, 354.9 mmol), Pd (PPh3) 4 (2.7 g, and the mixture was refluxed for 2 put mol%) in a round bottom flask, tetrahydrofuran (THF) mixture gave after 3 hours poured (500ml) and H2O (250 ml). After the completion of the reaction remove the water layer and the organic layer with Mg3SO4 After dried under reduced pressure distillation. Ethyl acetate was recrystallized by using the anti-solvent to dissolve the crude product in CHCl3 intermediate B-1 (53 g, yield: 91%; MS: [M + H] + = 497) was obtained.
88.5%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 60℃; for 3h;Inert atmosphere;	Under an argon atmosphere, 2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (14.8g, 34.9mmol), 4- ( 2-pyridyl) phenyl boronic acid ( 9.04g, 45.4mmol) and tetrakistriphenylphosphine palladium (808 mg, 0.699 mmol and), was suspended in tetrahydrofuran (250 mL), and heated to 60 C..This 10 wt% NaOH aqueous solution (40 mL, 105 mmol) was added dropwise slowly and stirred for 3 h.After allowing the mixture to cool to room temperature, water (90mL) was added to the reaction mixture, the precipitate was collected by filtration.The resulting precipitate was purified by recrystallization with toluene, the desired product 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl] -4,6-diphenyl-1,3, It was obtained 5-triazine of a white solid (yield 15.4g, 88.5% yield).

77.1%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In 1,2-dimethoxyethane; water; at 70℃; for 5h;Inert atmosphere;	Under a nitrogen stream, a solution of 2- (3-bromo-5-chlorophenyl) -4,6-diphenyl- 1,3,5-triazine (66.2 g, 156.7 mmol), 4- (2-pyridyl) phenylboronic acid 40.5 g, 203.5 mmol) and tetrahydrofuran (1000 mL) were added to a 2 L separable flask, and a 10% NaOH aqueous solution (136 g, 470 mmol) was added dropwise thereto over 5 minutes and then tetrakistriphenylphosphine palladium (2.72 g , 2.35 mmol), and the mixture was stirred at 70 C. for 5 hours. After cooling to room temperature, water (660 mL) was added to the reaction mixture, and the precipitate was collected by filtration. The precipitate collected by filtration was washed successively with pure water, methanol and hexane to obtain a gray powder. Subsequently, the obtained gray powder was purified by recrystallization from toluene to obtain the objective compound 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl] -4,6- diphenyl- An off white powder of 1,3,5-triazine (yield 60.0 g, yield 77.1%, LC purity 99.67%) was obtained.
77.1%		Under a nitrogen stream,2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (66.2 g, 156.7 mmol)4- (2-pyridyl) phenylboronic acid (40.5 g, 203.5 mmol),, And tetrahydrofuran (1000 mL) were added to a 2 L separable flask, and a 10% NaOH aqueous solution (136 g, 470 mmol) was added dropwise thereto over 5 minutes,Tetrakistriphenylphosphine palladium (2.72 g, 2.35 mmol) was added,And the mixture was stirred at 70 C. for 5 hours. After cooling to room temperature,Water (660 mL) was added to the reaction mixture, and the precipitate was collected by filtration. The collected precipitate was washed successively with pure water, methanol and hexane to obtain a gray powder. Thereafter, the obtained gray powder was purified by recrystallization with toluene to obtain an off-white powder (yield 60.0 g, yield 77.1%, LC purity 99.67%) of the object compound (B1) Obtained.The compound was identified by FDMS.FDMS: 496
60%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 85℃;Inert atmosphere;	Under argon flow, 2- (3-bromo-5-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (30.0 g, 71 mmol)4- (2-pyridyl) phenylboronic acid (21.2 g, 110 mmol),Tetrakis (triphenylphosphine) palladium (4.10 g, 3.6 mmol)It was suspended in toluene (710 mL)A 1.0 M aqueous solution of sodium carbonate (210 mL) was added dropwise,The mixture was stirred at 85 C for a while.After allowing to cool, methanol and water were added, the precipitated solid was filtered off, and the solid was washed with water, methanol and hexane.Further purification by recrystallization (toluene) gave a white color of the desired 2- [5-chloro-4 '- (2-pyridyl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine A solid (yield: 21.0 g, yield 60%) was obtained.

Reference： [1]Patent: JP2015/27986,2015,A .Location in patent: Paragraph 0345
[2]Patent: KR2016/90262,2016,A .Location in patent: Paragraph 0905-0907
[3]Patent: KR2016/32020,2016,A .Location in patent: Paragraph 0223 - 0225
[4]Patent: JP2015/38062,2015,A .Location in patent: Paragraph 0070
[5]Patent: JP2017/132734,2017,A .Location in patent: Paragraph 0059-0061
[6]Patent: JP2016/27040,2016,A .Location in patent: Paragraph 0200-0201

32
[ 170230-27-0 ]
3-[1-chloro-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl-3-yl]-9-(6-methylpyridin-2-yl)carbazole [ No CAS ]
9-(6-methylpyridin-2-yl)-3-[5-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(2-pyridyl)biphenyl-3-yl]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium acetate; palladium diacetate; potassium carbonate; XPhos; In water; toluene; butan-1-ol; for 6.5h;Inert atmosphere; Reflux;	Then, a stream of argon, 3- [1-chloro-5- (4,6-diphenyl-1,3,5-triazin-2-yl) - phenyl-3-yl] -9- (6-methylpyridin-- 2-yl) carbazole (1.80 g), 4- (2-pyridyl) phenylboronic acid (717 mg), palladium acetate (13.5 mg), and 2-dicyclohexyl phosphino-2 ', 4', 6'-tri isopropyl biphenyl (86 mg) was suspended in a mixed solvent of toluene (40 mL) and 1-butanol (3.0 mL), was added 3M- aqueous potassium carbonate solution (2.4 mL), it was heated under reflux for 6.5 hours. After cooling the reaction mixture was added water and methanol. The precipitated solid with water, methanol, washed with hexane, the purpose of 9- (6-methylpyridin-2-yl) -3- [5- (4,6-diphenyl-1,3,5-triazin-2 yl) -4 '- (2-pyridyl) biphenyl-3-yl] carbazole (compound the A-24)To obtain a gray powder (yield 2.00g, 93% yield).

Reference： [1]Patent: JP2015/27986,2015,A .Location in patent: Paragraph 0375

33
[ 170230-27-0 ]
7-phenyl-9-(pyridine-3-yl)-7H-benzo[c]carbazole-5-yl trifluoromethanesulfonate [ No CAS ]
7-phenyl-9-(pyridin-2-yl)-5-(4-(pyridin-2-yl)phenyl)-7H-benzo[c]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.4 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 1.5h;Inert atmosphere; Reflux;	Then, above the 7-phenyl-9- (pyridin-2-yl) obtained by -7H- benzo [c] carbazol-5-yl trifluoromethanesulfonate (2.8 g), (4- (pyridin 2-yl) phenyl) boronic acid (1.3 g), sodium carbonate (1.2g), Pd (PPh3) 4 (0.31g), containing toluene (12 ml), ethanol (4 ml) and water (4 ml) the flask, under a nitrogen atmosphere and stirred for 1.5 hours at reflux temperature. The reaction mixture was cooled to room temperature, and ethylene diamine tetra-acetic acid (EDTA) solution and ethyl acetate were added for liquid separation. Further, the organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. The resulting solid was purified by silica gel column chromatography and purified by (eluent toluene / ethyl acetate mixed solvent). At this time, gradually increasing the ratio of ethyl acetate in developing solution to elute the desired product. Thereafter, the solvent was a obtained was distilled off under reduced pressure and the solid was washed with ethyl acetate, a compound represented by the formula (1-541) 7-phenyl-9- (pyridin-2-yl) -5- (4- ( pyridin-2-yl) to yield phenyl)-7H-benzo [c] carbazole (0.4 g).

Reference： [1]Patent: JP5673362,2015,B2 .Location in patent: Paragraph 1136; 1137

34
[ 170230-27-0 ]
[ 942132-67-4 ]
[ 1268250-61-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tri-tert-butyl phosphine; palladium diacetate; sodium hydroxide; In tetrahydrofuran; water; toluene; for 9h;Inert atmosphere; Reflux;	Under an argon stream, 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine (10.0g), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (11.1g), palladium acetate (96.3mg) , tri-tert-butylphosphine toluene solution (1.29 mL), 4N sodium hydroxide aqueous solution (21.5 mL), were suspended in THF (190 mL), and heated under reflux for 9 h. After cooling the reaction, water was added. The precipitated solid was filtered off, washing with water and methanol afforded the target compound 2-[4,4"-di(2-pyridyl)-1,1'-:3',1"-terphenyl-5'-yl]-4,6-diphenylpyrimidine (ETL-1) as white powder (9.2g, 70% yield).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0066

35
[ 170230-27-0 ]
C₃₈H₂₃BrN₂ [ No CAS ]
4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.65 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 65℃; for 12h;	Then, <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (6.4 g), 1M potassium carbonate aqueous solution (32 mL) were added, and stirred for 12 h at 65 C. After cooling the reaction mixture, the solvent was evaporated under reduced pressure. The precipitated solid was filtered off, washed with water and methanol, dissolved in chloroform and by purification with silica gel chromatography (eluent chloroform) afforded the target compound 4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine (A-1) as yellow powder (8.65 g, 61% yield).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0055; 0057

36
[ 170230-27-0 ]
2-(3-bromo-5-chlorophenyl)-4,6-diphenylpyrimidine [ No CAS ]
4,6-diphenyl-2-[5-chloro-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; for 24h;Inert atmosphere; Reflux;	Under an argon stream, 2-(3-bromo-5-chlorophenyl)-4,6-diphenyl-pyrimidine (8.4 g), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (4.4 g), tetrakis(triphenylphosphine)palladium (328 mg), 4N aqueous sodium hydroxide solution (7.5 mL), were suspended in THF (100 mL) and heated to reflux for 24 h. After cooling, water was added to the reaction mixture was extracted with chloroform. The organic layer silica gel chromatography (developing solvent: chloroform) to give the target compound 4,6-diphenyl-2-[5-chloro-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine as a white powder (8.3g, 83% yield).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0053; 0054

37
[ 170230-27-0 ]
2-(3-bromo-5-chlorophenyl)-4,6-diphenylpyrimidine [ No CAS ]
4,6-diphenyl-2-[5-(9-anthracenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]

Reference： [1]Patent: JP2015/3899,2015,A

38
[ 170230-27-0 ]
4,6-diphenyl-2-[3-chloro-5-(1-pyrenyl)phenyl]pyrimidine [ No CAS ]
4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium diacetate; potassium carbonate; XPhos; In water; toluene; butan-1-ol; at 100℃; for 3h;Inert atmosphere;	Under a stream of argon, 4,6-diphenyl-2-[3-chloro-5-(1-pyrenyl)phenyl]pyrimidine (6.5 g), <strong>[170230-27-0]4-(2-pyridyl)phenylboronic acid</strong> (2.9 g), palladium acetate (26.9mg), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (171mg), 3M aqueous potassium carbonate solution (9.6mL), were suspended in a mixed solvent of toluene (54mL) and 1-butanol (6.0 mL), and stirred for 3 h at 100 C. After cooling the reaction, water was added and methanol. The precipitated solid was filtered off, washing with water and methanol gave the target compound 4,6-diphenyl-2-[5-(1-pyrenyl)-4'-(2-pyridyl)biphenyl-3-yl]pyrimidine (A-1) as yellow powder (7.53 g, 98% yield).; Purification Example - 1 Heating the yellow powder Compound A-1 (8.26g) to 350 C under 1.0×10-3 Pa vacuum to purify by sublimation afforded yellow powder Compound A-1 (7.33 g, 89% yield, 99% or higher purity).

Reference： [1]Patent: JP2015/3899,2015,A .Location in patent: Paragraph 0058; 0059; 0067

39
[ 170230-27-0 ]
4,6-diphenyl-2-[4'-(2-pyridyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-yl]-1,3,5-triazine [ No CAS ]

Reference： [1]Patent: KR2016/32020,2016,A
[2]Patent: KR2016/90262,2016,A
[3]Patent: JP2017/132734,2017,A

40
[ 170230-27-0 ]
2-{3-[4-(adamantan-1-yl)phenyl]-5-[4-(pyridin-2-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine [ No CAS ]

Reference： [1]Patent: KR2016/32020,2016,A

41
[ 170230-27-0 ]
C₂₅H₁₆BrN₃ [ No CAS ]
C₃₆H₂₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	Formula 1D (10g, 22.8mmol) and pyridine-phenyl boronic acid (4.5g, 22.8mmol) and potassium carbonate (K2CO3) (9.5g, 68.4mmol) in tetrahydrofuran (THF) (200mL), H2O (70ml) dissolved in It was heated to 90C . After addition of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) (0.8g, 0.68mmol) was refluxed for 4 hours. After cooling to room temperature to remove the water layer. After loading the hwangsang magnesium (MgSO4) the organic layer was filtered. After concentration and purification by column chromatography to obtain the compound of Formula 5-11-1 (8g, 68% yield).

Reference： [1]Patent: KR101553169,2015,B1 .Location in patent: Paragraph 0537; 0544; 0545

42
[ 170230-27-0 ]
C₃₅H₂₀F₉N₃O₃S [ No CAS ]
C₄₂H₂₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	General procedure: Dissolved in Formula 1B (16g, 21.8mmol) and diphenyl-pyridine beam Rolando (10.4g, 24mmol) and potassium carbonate (K2CO3) (9g, 65.2mmol) in tetrahydrofuran (THF) (300mL), H2O (100ml) It was heated to 90C. After addition of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) (0.5g, 0.43mmol) was refluxed for 4 hours. After cooling to room temperature to remove the water layer. After loading the hwangsang magnesium (MgSO4) the organic layer was filtered. After concentration is purified by column chromatography to obtain the compound of Formula 2-1-1 (11g, 68% yield).In the manufacture of Formula 2-1-1 of the above Synthesis Example 1, diphenyl-pyridine-dioxo-beam instead Rolando, pyridine compounds, except for using phenylboronic acid (9.6g, 48mmol) and the formula was prepared in the same manner as 2- 1-2 was obtained (20g, yield 78%).

Reference： [1]Patent: KR101553169,2015,B1 .Location in patent: Paragraph 0426; 0428-0432

43
[ 170230-27-0 ]
C₅₀H₃₃N₅ [ No CAS ]

Reference： [1]Patent: KR2016/90262,2016,A

44
[ 170230-27-0 ]
C₄₄H₂₉N₅ [ No CAS ]

Reference： [1]Patent: KR2016/90262,2016,A

45
[ 1073062-42-6 ]
[ 170230-27-0 ]
4,6-diphenyl-2-(4'-(2-pyridyl)-5-(triphenylene)biphenyl-3-yl)-1,3,5-triazine [ No CAS ]

Reference： [1]Patent: JP2015/38062,2015,A

46
[ 5467-74-3 ]
[ 170230-27-0 ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

47
[ 170230-27-0 ]
[ 583-53-9 ]
2-(2'-bromo-[1,1'-biphenyl]-4-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 110℃; for 16h;Inert atmosphere; Schlenk technique;	(3) Under a nitrogen atmosphere,2.80 g (14.0 mmol) of compound 2 was weighed,0.81 g (0.70 mmol) of catalyst Pd (PPh3) 4Was added to the SCHLENK reaction tube,3.32 g (14.0 mmol) of o-dibromobenzene was added,Degassed 30 mL of tetrahydrofuran (THF) and 20 mLPotassium carbonate (K2CO3) solution (2M)The temperature was raised to 110 C and the reaction was stirred for 16 hours.He reacted with a mixture of methylene chloride (CH2C12) extracted,The organic phase was dried over anhydrous sodium sulphate (Na2SO4) and concentrated,The residue was purified by silica gel column chromatography,The mobile phase was PE: Et2O = 5: 1 (V / V, Et2O = diethyl ether)To give 3.12 g (yield 71.5%) of a white solid,By NMR characterization,The product was the target product 3:

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A .Location in patent: Paragraph 0029; 0030; 0033

48
[ 63996-36-1 ]
[ 121-43-7 ]
[ 170230-27-0 ]

Yield	Reaction Conditions	Operation in experiment
65.8%		(2) Weigh 5.0 g (21.36 mmol) of compound 1 in a three-30 mL of anhydrous tetrahydrofuran (THF) was added by a syringe under a nitrogen atmosphere,The temperature of the system was lowered to -78 C using an acetone / liquid nitrogen bath,11.2 mL (2.5 M) of n-BuLi (n-BuLi) solution was slowly added dropwise with a syringe,The reaction was stirred at -78 C for 1 hour.Under nitrogen atmosphere, 7.4 mL (64.08 mmol)(B (OMe) 3),Remove the acetone / liquid nitrogen bath,The reaction was stirred at room temperature for 16 hours.Water quenching reaction,The mixture was extracted with dichloromethane (CH2Cl2)The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated.With petroleum ether precipitation, a white solid precipitation,The filter cake was filtered and vacuum dried,To give 2.80 g (yield 65.8%) of a white solid,By NMR characterization,The product was the target product 2:

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A .Location in patent: Paragraph 0029; 0030; 0032

49
[ 170230-27-0 ]
phenyl(4'-(pyridin-2-yl)-[1,1'-biphenyl]-2-yl)phosphine oxide [ No CAS ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

50
[ 170230-27-0 ]
5-phenyl-3-(pyridin-2-yl)benzo[b]phosphindole-5-oxide [ No CAS ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

51
[ 170230-27-0 ]
C₄₅H₃₄IrN₂O₄P [ No CAS ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

52
[ 170230-27-0 ]
C₅₇H₅₁BIrN₂O₃P [ No CAS ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

53
[ 109-04-6 ]
[ 170230-27-0 ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 8556 - 8569
[2]Patent: CN105859793,2016,A

54
[ 170230-27-0 ]
C₅₁H₃₉IrN₃O₃P [ No CAS ]

Reference： [1]Patent: CN105859793,2016,A

55
[ 170230-27-0 ]
(S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
ethyl (2S)-2-(tert-butoxy)-2-[4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-[4-(pyridin-2-yl)phenyl]pyridin-3-yl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.9%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 110℃; for 2h;Inert atmosphere;	(S)-Ethyl 2-(tert-butoxy)-2-(4-(4, 4-dimethylpiperidin-l-yl)-2, 6-dimethyl-5-(4-(pyridin-2- yl)phenyl)pyridin-3-yl)acetate: A mixture of (S)-ethyl 2-(5-bromo-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.042 g, 0.092 mmol), <strong>[170230-27-0](4-(pyridin-2-yl)phenyl)boronic acid</strong> (0.028 g, 0.138 mmol) and 2M Na2C03 (0.1 15 ml, 0.231 mmol) in DMF (2 mL) degassed for 10 min. Then, Pd(Ph3P)4 (10.66 mg, 9.22 mupiiotaomicron) was added, degassed for 5 min and placed in a pre-heated oil bath at 1 10 C. After 2 h, cooled and purified by pre-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(4- (4,4-dimethylpiperidin-l-yl)-2,6-dimethyl-5-(4-(pyridin-2-yl)phenyl)pyridin-3-yl)aceta^ (0.0244 g, 0.046 mmol, 49.9 % yield) as white solid. 1H NMR (500 MHz, CDC13) delta 8.74-8.77 (m, IH), 8.11 (ddd, J=1.7, 7.9, 16.7 Hz, 2H), 7.79-7.86 (m, 2H), 7.42 (dd, J=1.6, 7.9 Hz, IH), 7.29-7.32 (m, 2H), 6.09 (s, IH), 4.28 (qd, 7=7.1, 10.7 Hz, IH), 4.20 (qd, 7=7.1, 10.8 Hz, IH), 3.25 (d, 7=11.5 Hz, IH), 2.93 (t, 7=12.1 Hz, IH), 2.63 (s, 3H), 2.34 (d, 7=11.7 Hz, IH), 2.23 (s, 3H), 2.14 (t, 7=11.3 Hz, IH), 1.52-1.58 (m, IH), 1.34- 1.42 (m, IH), 1.28 (t, 7=7.3 Hz, 3H), 1.22 (s, 9H), 1.18 (br. s., IH), 1.04-1.10 (m, IH), 0.89 (br. s., 3H), 0.62 (s, 3H). LCMS (M+H) = 530.3.

Reference： [1]Patent: WO2017/6281,2017,A1 .Location in patent: Page/Page column 59-60

56
[ 170230-27-0 ]
[ 6710-92-5 ]
[ 86-74-8 ]
C₄₁H₂₄N₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		0.2 mol of carbazole and 0.1 mol of trichlorotris triazine were added to 500 mL of toluene,After stirring at room temperature for 6 hours,The solvent was removed by suction filtration,The resulting precipitate was reintroduced into a new 500 mL of toluene,Then add 200mL ethanol,300mL sodium carbonate solution with a concentration of 2mol / L,0.1 mmol of tetrakis (triphenylphosphine) palladium,0.15 mol of 4- (2-pyridyl) -benzeneboronic acid,Under nitrogen protection conditions, the reaction was carried out at 100 C for 24 hoursThe After cooling, the mixture was extracted with ethyl acetate, and the solvent was removed by spin filtration to obtain the title compound (I-8) by chromatography. The reaction yield was 19%

Reference： [1]Patent: CN106883240,2017,A .Location in patent: Paragraph 0121; 0122; 0123; 0124

57
[ 170230-27-0 ]
C₄₅H₂₉N₅ [ No CAS ]

Reference： [1]Patent: JP2017/132734,2017,A

58
[ 170230-27-0 ]
C₄₀H₂₆ClN₃ [ No CAS ]
C₅₁H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux; Inert atmosphere;	Under a nitrogen atmosphere, compound C (11.17 g, 19.16 mmol),(4- (pyridin-2-yl) phenyl) boronic acid(4.38 g, 22.03 mmol) was completely dissolved in 220 ml of tetrahydrofuran and 2M aqueous potassium carbonate solution (110 ml) was added. Tetrakis (triphenylphosphine) palladium (0.66 g, 0.57 mmol) was added and the mixture was stirred under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Recrystallization from 210 ml of ethyl acetate yielded Compound 7 (8.47 g, 63%).

Reference： [1]Patent: CN107353281,2017,A .Location in patent: Paragraph 0288; 0289; 0290; 0291

59
[ 170230-27-0 ]
C₄₂H₂₈ClN₃ [ No CAS ]
C₅₃H₃₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 18h;Inert atmosphere;	10189] Intermediate 1-7 (10 g, 16.4 mmol) was dissolved in tetrahydroffiran (THF, 0.1 L) under a nitrogen environment, 4-(pyridin-2-yl)phenylboronic acid (3.26 g, 16.4 mmol, purchased from Changsha Luxing Bio-chem Tech Co., Ltd. (http://www.luxingbc.coml)), tetrakis(triphenylphosphine)palladium (0.18 g, 0.16 mmol), and potassium carbonate saturated in water (5.67 g, 41.0 mmol) were added thereto, and the mixture was heated and refluxed at 80 C. for 18 hours. Afier the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichioromethane (DCM) and treated with anhydrous Mg504 to remove moisture, and the resultant was filtered and concentrated under a reduced pressure. A residue obtained therefrom was separated and purified through flash column chromatography to obtain Compound 26 (8.25 g, 69%).HRMS (70 eV, EI+): mlz calcd for C53H36N4:728.2940, found: 728Elemental Analysis: C, 87%; H, 5%

Reference： [1]Patent: US2017/373255,2017,A1 .Location in patent: Paragraph 0188; 0189; 0190; 0191

60
[ 170230-27-0 ]
2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4"-di(2-pyridyl)-1,1':4',1"-terphenyl [ No CAS ]