[ CAS No. 107351-82-6 ] {[proInfo.proName]}

Name: 107351-82-6|2-Bromo-5-phenylpyridine|97%
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Quality Control of [ 107351-82-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 107351-82-6 ]

Product Details of [ 107351-82-6 ]

CAS No. :	107351-82-6	MDL No. :	MFCD04114195
Formula :	C₁₁H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TVOAXRDXTGCPBB-UHFFFAOYSA-N
M.W :	234.09	Pubchem ID :	2762875
Synonyms :

Calculated chemistry of [ 107351-82-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.37
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.38
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.7
Consensus Log Po/w :	3.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.11
Solubility :	0.018 mg/ml ; 0.000077 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.45
Solubility :	0.0823 mg/ml ; 0.000352 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.4
Solubility :	0.00093 mg/ml ; 0.00000397 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 107351-82-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 107351-82-6 ]

* 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 [ 107351-82-6 ]

[ 107351-82-6 ] Synthesis Path-Downstream 1~49

1
[ 624-28-2 ]
[ 108-86-1 ]
[ 15827-72-2 ]
[ 27012-25-5 ]
[ 107351-82-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 386 - 390

2
[ 33421-40-8 ]
[ 107351-82-6 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3621 - 3630
[2]Journal of Organic Chemistry,2009,vol. 74,p. 5228 - 5236
[3]Heterocycles,1986,vol. 24,p. 1815 - 1819
[4]Monatshefte fur Chemie,2003,vol. 134,p. 573 - 583
[5]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1641 - 1649

3
[ 107351-82-6 ]
[ 74-89-5 ]
[ 107351-83-7 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1815 - 1819
[2]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1641 - 1649

4
[ 108-86-1 ]
[ 223463-14-7 ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890

5
[ 108-86-1 ]
[ 214360-62-0 ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890

6
[ 1008-88-4 ]
[ 107351-82-6 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2028 - 2029
[2]Heterocycles,1986,vol. 24,p. 1815 - 1819

7
[ 76053-45-7 ]
[ 107351-82-6 ]

Reference： [1]Monatshefte fur Chemie,2003,vol. 134,p. 573 - 583

8
[ 73290-22-9 ]
[ 98-80-6 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 120℃; for 4h;	2-Bromo-5-iodopyridine (4.4g, 16mmol) was dissolved in toluene (70ml). To this solution benzene boronic acid (2.6g, 20mmol) was added-, followed by aqueous K2C03 (8. 5M, 70ml) and Pd (Ph3P) 4 (23mg, 0. 02mmol). The mixture was vigorously stirred at 120C for 4 days. The solvent was evaporated in vacuo and the residue was purified by column chromatography to give 2-bromo-5-phenyl-pyridine (3. 5g, 93%).
79.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 60℃; for 3h;Inert atmosphere;	Synthesis of Intermediate 14-A: Under nitrogen protection, To a 500 mL three-neck round bottom flask, was added 2-bromo-5-iodopyridine (14.20g, 0.05mol), phenylboronic acid (11.9g, 0.06mol),2.88g (0.0025mol) Pd (PPh3) 4,80ml of toluene, 80ml of ethanol, and 50ml concentration 2mol·L-1 potassium carbonate solution, and the reaction stirred for 3h at 60 C. After cooling, the organic phase was separated,The organic phase was washed with water three times and dried over anhydrous Mg2SO4, organic solvent removed by rotary evaporation to obtain a crude product. The crude product was purified by column chromatography on silica gel to give a white crystalline solid 9.31g.
12.4 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux;	In a 1 L reaction vessel Intermediate A-3 (25 g), Phenylboronic acid (10.74 g), & lt; RTI ID = 0.0 & gt; Pd (PPh3) 4 (3.05 g), K2CO3 (24.3 g) , THF (333 mL) and distilled water (166 mL) were put together, And refluxed under nitrogen for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the aqueous layer was removed. The organic layer was washed with 5% brine (500 mL) And once with distilled water (500 mL). The organic layer obtained was dried over MgSO4, the solvent was removed, and ethyl acetate: n-hexane (= 3: 97) The residue was purified by silica gel column chromatography Purification yielded intermediate A-2 (12.4 g).

Reference： [1]Patent: WO2005/92304,2005,A2 .Location in patent: Page/Page column 42
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 15545 - 15549
Angew. Chem.,2015,vol. 127,p. 15766 - 15770,5
[3]Patent: CN102977129,2016,B .Location in patent: Paragraph 0124; 0125
[4]Patent: KR2015/131882,2015,A .Location in patent: Paragraph 0299; 0302-0304

9
[ 1072-97-5 ]
[ 107351-82-6 ]

Reference： [1]Monatshefte fur Chemie,2003,vol. 134,p. 573 - 583

10
[ 98-80-6 ]
polymer; monomer(s): Actitex 1500-1, modified with [BF₄][4-N₂C₆H₄CH₂Cl]; 4-halogenobenzenethiol [ No CAS ]
[ 107351-82-6 ]

Reference： [1]Monatshefte fur Chemie,2003,vol. 134,p. 573 - 583

11
[ 504-29-0 ]
3-iodobenzyl 4-hydroxybenzoic acid coupled to N-methyl aminomethylated polystyrene [ No CAS ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890
[2]Tetrahedron,2002,vol. 58,p. 2885 - 2890

12
[ 20511-12-0 ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890
[2]Tetrahedron,2002,vol. 58,p. 2885 - 2890

13
[ 624-28-2 ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890
[2]Tetrahedron,2002,vol. 58,p. 2885 - 2890

14
[ 73290-22-9 ]
[ 107351-82-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890
[2]Tetrahedron,2002,vol. 58,p. 2885 - 2890

15
[ 107351-82-6 ]
2-amino-3-methyl-6-phenyl-1H-imidazo<4,5-b>pyridine [ No CAS ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1815 - 1819

16
[ 107351-82-6 ]
[ 107351-85-9 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1815 - 1819

17
[ 107351-82-6 ]
[ 107351-86-0 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1815 - 1819

18
[ 107351-82-6 ]
Methyl-[5-(4-nitro-phenyl)-pyridin-2-yl]-amine [ No CAS ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1815 - 1819

19
[ 591-50-4 ]
[ 225932-26-3 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
30%	tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 24h;	191 mul of iodobenzene (1.1 equivalents) and 53.9 mg of tetrakis(triphenylphosphine)palladium(0) (0.03 equivalent) are added to a solution of 0.5 g of the substrate obtained in the preceding Stage 1 in 5.0 ml of degassed DME. The reaction medium is stirred at 80 C. for 24 hours and is then diluted with ethyl acetate (75 ml). The organic phase is washed with water (3×30 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. Chromatography of the residue on silica gel (dichloromethane: 100%) makes it possible to isolate 110.3 mg of the expected product. Yield: 30% 1H NMR (DMSO) delta (ppm): 8.70 (m, 1H), 8.05 (m, 1H), 7.75 (m, 3H), 7.50 (m, 3H)

Reference： [1]Patent: US2004/72871,2004,A1 .Location in patent: Page/Page column 24

20
[ 107351-82-6 ]
2-(5-Phenyl-pyridin-2-yl)-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 56 2-(5-Phenyl-pyridin-2-yl)-propionic acid methyl ester STR209 The desired compound was obtained from <strong>[107351-82-6]2-bromo-5-phenylpyridine</strong> (M. G. Knize, et al., Heterocycles, 24, 1815 (1986)) by the known method described in T. Sakamoto, et al., Heterocycles, 36, 2509 (1993). 1 H-NMR (270 MHz, CDCl3) delta ppm: 1.61(d, 3H, J=7.3 Hz), 3.72(s, 3H), 4.01(q, 1H, J=7.3 Hz), 7.34-7.59(m, 6H, 7.85 (dd, 1H, J=8.2, 2.3 Hz), 8.78(d, 1H, J=2.3 Hz)

Reference： [1]Patent: US6100260,2000,A

21
[ 927898-18-8 ]
[ 107351-82-6 ]
[ 927898-40-6 ]

Yield	Reaction Conditions	Operation in experiment
91%		EXAMPLE 5 Synthesis of 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine Under a stream of argon, 3.5 ml of a pentane solution containing 5.2 mmol of tert-butyl lithium was slowly added to 15 ml of tetrahydrofuran cooled to -78C, and 10 ml of tetrahydrofuran in which 0.61 g of <strong>[107351-82-6]2-bromo-5-phenylpyridine</strong> had been dissolved was further added dropwise to this solution. After stirring at -78C for 30 minutes, 1.64 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at -78C for 10 minutes and then at room temperature for 2 hours. A 35 ml portion of tetrahydrofuran prepared by dissolving 1.00 g of 2-(4-bromophenyl)-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine synthesised by the method of Reference Example 1 and 0.12 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 10 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:dichloromethane = 3:2 to 4:3) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine (1.05 g, yield 91%). Its melting point is shown in Table 4. In this case, a distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 1.45 (s, 18H), 7.44-7.60 (m, 3H), 7.65 (d, J=8.6 Hz, 4H), 7.88 (d, J=8,5 Hz, 2H), 7.88-7.94 (m, 1H), 8.07-8.15 (m, 3H), 8.74 (d, J=8.6 Hz, 4H), 8.93 (d, J=8.5 Hz, 2H), 9.09 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 31.2, 35.1, 120.3, 125.6, 126.9, 127.0, 128.8, 129.1, 129.6, 133.6, 134.1, 135.1, 136.2, 138.8, 141.2, 148.1, 156.1, 156.6, 170.9, 171.5.

Reference： [1]Patent: EP1930329,2008,A1 .Location in patent: Page/Page column 26

22
[ 877456-08-1 ]
[ 107351-82-6 ]
[ 927898-38-2 ]

Yield	Reaction Conditions	Operation in experiment
8%		EXAMPLE 3 Synthesis of 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine Under a stream of argon, 3.0 ml of a hexane solution containing 4.2 mmol of butyl lithium was slowly added to 80 ml of tetrahydrofuran cooled to -78C in which 1.58 g of 2-(4-bromophenyl)-4,6-di-m-tolyl-1,3,5-triazine obtained in Reference Example 2 had been dissolved. After stirring at -78C for 15 minutes, 0.87 g of trimethyltin chloride was added thereto and stirred at -78C for 45 minutes and then at room temperature for 30 minutes. After evaporating and drying tetrahydrofuran under a reduced pressure, 120 ml of toluene in which 1.07 g of <strong>[107351-82-6]2-bromo-5-phenylpyridine</strong> had been dissolved and 0.44 g of tetrakis(triphenylphosphine)palladium(0) were added to the thus obtained solid and stirred under heating reflux for 3 days. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:chloroform = 3:2 to 1:1) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine (0.14 g, yield 8%). Its melting point is shown in Table 4. Distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 2.48 (s, 6H), 7.33-7.51 (m, 7H), 7.56-7.64 (m, 2H), 7.84-7.99 (m, 2H), 8.21 (d, J=8.5 Hz, 2H), 8.49-8.58 (m, 4H), 8.84 (d, J=8.6 Hz, 2H), 8.95 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 21.6, 120.9, 126.3, 127.0, 127.1, 128.3, 128.6, 129.2, 129.5, 133.3, 135.3, 135.6, 136.2, 136.9, 137.4, 138.3, 142.4, 148.2, 155.2, 171.2, 171.8.

Reference： [1]Patent: EP1930329,2008,A1 .Location in patent: Page/Page column 25

23
[ 107351-82-6 ]
2-halogeno-5-[(trimethylsilyl)ethynyl]pyridine [ No CAS ]
[ 1133486-50-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5228 - 5236

24
[ 127-19-5 ]
[ 107351-82-6 ]
[ 866326-59-2 ]

Yield	Reaction Conditions	Operation in experiment
54%		2-Bromo-5-phenyl-pyridine (2.2g, 9mmol) was added to dry diethyl ether (250ml). The mixture was cooled to-60C and a solution of n-BuLi (2. 5M in hexane, 4mL) was added dropwise and the mixture was stirred for 2hrs. N, N-dimethylacetamide (lmL) in diethyl ether (15ml) was then added slowly dropwise and the solution was left to stir for 3hrs. The system was brought to room temperature, hydrolysed with 2N HCl and extracted with DCM. The organic phase was washed with water, dried over MgS04 and evaporated to give 1- (5-phenyl-pyridin-2-yl)-ethanone (l. Og, 54%).

Reference： [1]Patent: WO2005/92304,2005,A2 .Location in patent: Page/Page column 41

25
[ 591-50-4 ]
[ 223463-14-7 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; N,N-dimethyl-formamide;tetrakis(triphenylphosphine) palladium(0); at 60℃; for 4h;	2-bromo-5-phenylpyridine. Na2CO3 (1.117 mL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2-bromopyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60 C. for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M+H)+ (Rt 1.72 min).
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 60℃; for 4h;	Na2CO3 (1.117 mL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2- bromorhoyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60 0C for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M + H)+ (Rt 1.72 min).
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 60℃; for 4h;	Na2CO3 (1.117 niL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2- bromopyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60 0C for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M + H)+(Rt 1.72 min).

Reference： [1]Patent: US2010/81643,2010,A1 .Location in patent: Page/Page column 40
[2]Patent: WO2010/47982,2010,A1 .Location in patent: Page/Page column 82
[3]Patent: WO2010/51206,2010,A1 .Location in patent: Page/Page column 83-84

26
[ 73290-22-9 ]
[ 108-86-1 ]
[ 107351-82-6 ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 5625 - 5641

27
[ 107351-82-6 ]
[ 182319-00-2 ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 5625 - 5641

28
[ 624-28-2 ]
[ 98-80-6 ]
[ 27012-25-5 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
86%; 12%	With potassium phosphate; palladium diacetate; triphenylphosphine; In methanol; acetonitrile; at 50℃; for 24h;Inert atmosphere;	General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10996 - 11003

29
[ 624-28-2 ]
[ 98-80-6 ]
[ 15827-72-2 ]
[ 27012-25-5 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
12%; 73%; 13%	With palladium diacetate; triphenylphosphine; potassium hydroxide; In methanol; acetonitrile; at 50℃; for 24h;Inert atmosphere;	General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10996 - 11003

30
[ 624-28-2 ]
[ 603-33-8 ]
[ 15827-72-2 ]
[ 27012-25-5 ]
[ 107351-82-6 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 5214 - 5228

31
[ 73290-22-9 ]
[ 603-33-8 ]
[ 33397-21-6 ]
[ 107351-82-6 ]
2-(4'-methoxyphenyl)-5-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%; 35%		General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 2-bromo-5-iodopyridine (0.875 mmol, 248.4 mg), bi(p-anisyl)3 (0.25 mmol, 132.6 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.02 mmol, 4.5 mg), PPh3 (0.08 mmol, 20.9 mg), and DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1 h. For the second coupling, tri(p-tolyl)bismuth (0.25 mmol, 120.5 mg), K3PO4 (1 mmol, 212.3 mg), and DMF (3 mL) were added to the Schlenk tube under nitrogen and the stirring was continued at 90C for 2 h. It was worked up following the procedure given in 4.2.1. After column chromatography separation, compounds 4.2 (160mg, 81%) and 5.1 (25mg, 12%) were obtained as white solids.

Reference： [1]Tetrahedron,2015,vol. 71,p. 338 - 349

32
[ 73290-22-9 ]
[ 603-33-8 ]
[ 107351-82-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

Reference： [1]Tetrahedron,2015,vol. 71,p. 338 - 349

33
[ 107351-82-6 ]
[ 1261628-25-4 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 15545 - 15549
Angew. Chem.,2015,vol. 127,p. 15766 - 15770,5

34
[ 107351-82-6 ]
methyl 2-bromo-2-(5-phenylpyridin-2-yl)acetate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 15545 - 15549
Angew. Chem.,2015,vol. 127,p. 15766 - 15770,5

35
[ 107351-82-6 ]
methyl 3-methoxy-10-phenyl-5,6-dihydrobenzo[g]pyrido[1,2-a]indole-7-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 15545 - 15549
Angew. Chem.,2015,vol. 127,p. 15766 - 15770,5

36
[ 107351-82-6 ]
[ 108-59-8 ]
dimethyl 2-(5-phenylpyridin-2-yl)malonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 15545 - 15549
Angew. Chem.,2015,vol. 127,p. 15766 - 15770,5

37
[ 5419-55-6 ]
[ 107351-82-6 ]
5‐phenylpyridin‐2‐ylboronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.7%	With n-butyllithium; In tetrahydrofuran; at -78℃;	Synthesis of Intermediate 14-B: Under nitrogen, in 250ml three-neck round bottom flask, Intermediate 14-A (7.02g, 0.03mol), and 120ml dried THF that underwent treatment with by Na / benzophenone were added. Liquid nitrogen was used to cool to -78C, then slowly added dropwise with stirring 14.5ml of n-butyllithium (0.036mol, 2.5mol·L-1), triisopropyl borate 9.96ml (8.12g, 0.043mol). After stirring to room temperature. Addition of an appropriate amount of dilute hydrochloric acid was added, extracted with ethyl acetate,The combined organic phases, the organic solvent was removed by rotary evaporation to give the crude product. And through recrystallization from ethanol as a white solid 3.92g, yield 65.7%.

Reference： [1]Patent: CN102977129,2016,B .Location in patent: Paragraph 0124; 0126

38
[ 107351-82-6 ]
C₄₉H₃₅BN₂ [ No CAS ]

Reference： [1]Patent: CN102977129,2016,B

39
[ 51-17-2 ]
[ 107351-82-6 ]
1-(5-phenylpyridin-2-yl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.98 g	With 1,2,3-Benzotriazole; copper(l) iodide; potassium tert-butylate; In dimethyl sulfoxide; for 12h;Reflux; Inert atmosphere;	A 100 mL reaction vessel was charged with intermediate A-2 (10 g), Benzimidazole (5 g), KOt-Bu (6.7 g), CuI (0.4 g), Benzotriazole (0.5 g) and dimethylsulfoxide (50 mL) were put together and refluxed under nitrogen for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and ethyl acetate (1 L) and 0.1 N HCl aqueous solution (1 L) were poured into the flask. The organic layer was separated and washed with 5% brine (1 L). The resulting organic layer was dried over MgSO4, the solvent was removed, and the residue was purified by silica gel column chromatography using an EA: n-hexane (50:50) solvent to obtain Intermediate A-1 (4.98 g).

Reference： [1]Patent: KR2015/131882,2015,A .Location in patent: Paragraph 0299; 0300; 0302; 0306; 0307

40
[ 10544-63-5 ]
[ 107351-82-6 ]
C₁₇H₁₉NO₂ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 3121 - 3125

41
3,5‐bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenol [ No CAS ]
[ 107351-82-6 ]
C₂₈H₂₀N₂O [ No CAS ]

Reference： [1]Patent: US2018/212158,2018,A1 .Location in patent: Paragraph 0565

42
[ 107351-82-6 ]
[ 25364-44-7 ]
C₂₃H₂₂N₃⁽¹⁺⁾*Br^(1-) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1088 - 1093
Angew. Chem.,2019,vol. 131,p. 1100 - 1105,6

43
[ 107351-82-6 ]
[ 25364-44-7 ]
C₅₀H₄₈N₈Ru⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1088 - 1093
Angew. Chem.,2019,vol. 131,p. 1100 - 1105,6

44
[ 1204186-62-8 ]
[ 107351-82-6 ]
C₄₁H₂₇N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; ethylenediamine; In toluene; for 24h;Reflux;	General procedure: Intermediate M1 (43.6 g, 0.1 mol), iodobenzene (24.5 g, 0.12 mol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol), ethylenediamine (2.3 ml, 34.3 mmol) and toluene (500 ml) were mixed.After stirring for 1 day under reflux, after the reaction was completed, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate (EA) and distilled under reduced pressure. the obtained distillation residue was subjected to column separation (eluent: EA/hexane), compound A1 (35.7 g, 70.1%) was obtained.

Reference： [1]Patent: CN109096281,2018,A .Location in patent: Paragraph 0053-0057; 0086-0089

45
[ 107351-82-6 ]
[ 98-80-6 ]
[ 15827-72-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	With palladium diacetate; potassium carbonate; triphenylphosphine; In methanol; acetonitrile; at 65℃; for 24h;Inert atmosphere;	General procedure: Method B: The preparation of 2-Bromopyridines with arylboronic acids was according to literature procedures.[1] To a 50-mL fire-dried flask was charged with 2-Bromopyridines (5 mmol, 1.0 eq), arylboronic acid (5.5 mmol, 1.5 eq), K2CO3 (1.38 g, 10.0 mmol, 2.0 eq), Pd(OAc)2 (56.0 mg, 0.25 mmol, 5.0 mol% ), PPh3 (131.0 mg, 0.5 mmol, 10.0 mol% ), CH3CN (10.0 mL) and methanol (5.0 mL). The mixture was degassed through a freeze-thaw-pump thread for three times. The reaction was stirred at 65 C for 24 hours. To the reaction mixture was added brine (15 mL) and ethyl acetate (15 mL). The phase was separated and the aqueous phase was extracted with ethyl acetate (4 × 15 mL). The combined organic phase was dried over Na2SO4 and concentrated under vacuum. The product was isolated by flash-column chromatography on silica gel (300-400 mesh).

Reference： [1]Tetrahedron,2019,vol. 75,p. 2547 - 2552
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 15244 - 15248
Angew. Chem.,2019,vol. 131,p. 15388 - 15392,5

46
[ 107351-82-6 ]
[ 98-80-6 ]
5-phenyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine [ No CAS ]

Reference： [1]Tetrahedron,2019,vol. 75,p. 2547 - 2552

47
[ 107351-82-6 ]
C₁₇H₁₃NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 15244 - 15248
Angew. Chem.,2019,vol. 131,p. 15388 - 15392,5

48
[ 107351-82-6 ]
5-phenyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 15244 - 15248
Angew. Chem.,2019,vol. 131,p. 15388 - 15392,5

49
[ 75754-04-0 ]
[ 107351-82-6 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 5565 - 5570

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P342	If experiencing respiratory symptoms:
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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H316	Causes mild skin irritation
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H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 107351-82-6 ] {[proInfo.proName]}

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[ 107351-82-6 ] Synthesis Path-Downstream 1~49

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Aryls

Bromides

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Pyridines

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