[ CAS No. 4373-60-8 ]

Name: 4373-60-8|2-(3-Bromophenyl)pyridine|95%
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Quality Control of [ 4373-60-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 4373-60-8 ]

CAS No. :	4373-60-8	MDL No. :	MFCD09749846
Formula :	C₁₁H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	234.09 g/mol	Pubchem ID :	11115506
Synonyms :

Calculated chemistry of of [ 4373-60-8 ]

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) :	-5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.82
Log Po/w (SILICOS-IT) :	3.7
Consensus Log Po/w :	3.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.0
Solubility :	0.0234 mg/ml ; 0.0001 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.27
Solubility :	0.127 mg/ml ; 0.000541 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 :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 4373-60-8 ]

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

Application In Synthesis of [ 4373-60-8 ]

* 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 [ 4373-60-8 ]
Downstream synthetic route of [ 4373-60-8 ]

[ 4373-60-8 ] Synthesis Path-Upstream 1~2

1
[ 110-86-1 ]
[ 10269-01-9 ]
[ 4422-32-6 ]
[ 4373-60-8 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2831 - 2835

2
[ 110-86-1 ]
[ 585-76-2 ]
[ 4422-32-6 ]
[ 4373-60-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 7, p. 2199 - 2203[2] Angew. Chem., 2014, vol. 54-127, # 7, p. 2227 - 2231

[ 4373-60-8 ] Synthesis Path-Downstream 1~42

1
[ 61676-62-8 ]
[ 4373-60-8 ]
[ 453530-49-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		A THF solution containing 2.51 g (10.7 mmol) of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> was cooled to -78 °C. To this solution was added 1 ml. portions of n-BuLi (1.6M in hexanes, 5.1 imL, 13 mmol) resulting in a dark green solution. After 45 min of stirring at -78 °C, 3.0 g (16 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane was added and stirred at -78 °C for 30 min. The dry ice bath was then removed, and the reaction was left to warm to room temperature overnight. The reaction was then quenched with MeOH (5 ml_), preabsorbed on silica, and the solvent was removed in vacuo. The sample was purified using chromatography [Si02: (DCM/EtOAc 9:1 ): Rf = 0.57] to afford 2.2 g (73percent) of a colorless oil. 1H NMR (400 MHz, CDCI3): delta=8.67 (ddd, 3J=5 Hz, J=2 Hz, 5J=1 Hz, 1 H, Ha), 8.37 (s, 1 H, He), 8.11 (ddd, 3J=8 Hz, J=2 Hz, 5J=1 Hz, 1 H, Hf), 7.84 (dt, 3J=8 Hz, 4J=1 Hz, 1H, Hh), 7.77 (dt, 3J=8 Hz, 4J=1 Hz, 1 H, Hd), 7.71 (dt, 3J=7 Hz, 4J=2 Hz, 1 H, Hc), 7.47 (t, 3J=8 Hz, H, Hg), 7.19 (ddd, 3J=7 Hz, 4J=5 Hz, 5J=1 Hz, 1 H,Hb), 1.34 (s, 12H, HMethyi); 3C NMR (100 MHz, CDCI3): delta = 157.7, 149.8, 139.0, 136.8, 135.5, 133.4, 130.0, 128.4, 122.2, 120.9, 84.1 ,25.1 ;HRMS (El): m/z = 281.1598 [(M)+] (calcd for Ci7H2oBN02+: m/z = 281.1587).

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 4960 - 4971
[2]Patent: WO2012/155247,2012,A1 .Location in patent: Page/Page column 59
[3]RSC Advances,2016,vol. 6,p. 41214 - 41218
[4]Macromolecules,2003,vol. 36,p. 9721 - 9730
[5]Dyes and Pigments,2011,vol. 90,p. 139 - 145

2
[ 452914-03-3 ]
[ 4373-60-8 ]
C₄₅H₅₃NO₂ [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 9721 - 9730

3
[ 5029-67-4 ]
[ 89598-96-9 ]
[ 4373-60-8 ]

Reference： [1]Journal of Materials Chemistry,2006,vol. 16,p. 4706 - 4713

4
[ 3240-34-4 ]
[ 4373-60-8 ]
4-bromo-2-(pyridin-2-yl)phenyl acetate [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4149 - 4152
[2]Organic Letters,2017,vol. 19,p. 6470 - 6473

5
[ 108-36-1 ]
[ 17997-47-6 ]
[ 4373-60-8 ]

Reference： [1]Dyes and Pigments,2011,vol. 90,p. 139 - 145
[2]Organic Letters,2005,vol. 7,p. 4149 - 4152
[3]RSC Advances,2016,vol. 6,p. 41214 - 41218

6
[ 852475-03-7 ]
[ 4373-60-8 ]
2-(4'-(triphenylsilyl)biphenyl-3-yl)pyridine [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2006,vol. 16,p. 4706 - 4713

7
[ 4373-60-8 ]
[ 453530-50-2 ]

Reference： [1]Macromolecules,2003,vol. 36,p. 9721 - 9730

8
[ 4373-60-8 ]
C₈₅H₁₀₁NO₄ [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 9721 - 9730

9
[ 877456-11-6 ]
[ 4373-60-8 ]
[ 927898-55-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		EXAMPLE 16 Synthesis of 2,4-bis(4-biphenylyl)-6-[3'-(2-pyridyl)biphenyl-4-yl]-1,3,5-triazine Under a stream of argon, 4.1 ml of a pentane solution containing 6.0 mmol of tert-butyl lithium was slowly added to 20 ml of tetrahydrofuran cooled to -78°C, and 10 ml of tetrahydrofuran in which 0.70 g of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> had been dissolved was further added dropwise to this solution. After stirring at -78°C for 30 minutes, 1.89 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at -78°C for 10 minutes and then at room temperature for 2 hours. A 50 ml portion of tetrahydrofuran prepared by dissolving 1.35 g of 2,4-bis(4-biphenylyl)-6-(4-bromophenyl)-1,3,5-triazine obtained in Reference Example 3 and 0.12 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 15 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was purified by a silica gel column chromatography (eluding solution hexane:chloroform = 2:1 to chloroform) and an alumina gel column chromatography (eluding solution hexane:chloroform = 2:1 to chloroform) and then recrystallized from dichloromethane-methanol and toluene to obtain a white solid of the intended 2,4-bis(4-biphenylyl)-6-[3'-(2-pyridyl)biphenyl-4-yl]-1,3,5-triazine (1.29 g, yield 84percent). 1H-NMR (CD2Cl2): S 7.32 (ddd, J=7.2, 4.8, 1.2 Hz, 1H), 7.41-7.45 (m, 2H), 7.50-7.55 (m, 4H), 7.63 (brdd, J=7.7, 7.7 Hz, 1H), 7.74-7.78 (m, 4H), 7.80-7.90 (m, 3H), 7.87 (d, J=8.5 Hz, 4H), 7.96 (d, J=8.5 Hz, 2H), 8.07 (ddd, J=7.7, 1.3, 1.2 Hz, 1H), 8.42-8.44 (m, 1H), 8.74 (ddd, J=4.8, 1.7, 1.0 Hz, 1H), 8.90 (d, J=8.5 Hz, 4H), 8.92 (d, J=8.5 Hz, 2H). 13C-NMR (CDCl3): delta 120.8, 122.4, 126.0, 126.6, 127.4, 127.4, 127.6, 127.9, 128.1, 129.0, 129.4, 129.6, 135.3, 135.4, 136.9, 140.2, 140.5, 141.1, 145.1, 145.3, 149.9, 157.3, 171.5.

Reference： [1]Patent: EP1930329,2008,A1 .Location in patent: Page/Page column 30

10
[ 73183-34-3 ]
[ 4373-60-8 ]
[ 453530-49-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 85℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, to a 250ml three-necked flask was added 3- (2-pyridyl) group bromobenzene (10.3g, 44.1mmol), United pinacolato ester (12.3 g , 48.5mmol, TCI), potassium acetate (13.0g, 133mmol), 1,1'- bis (diphenylphosphino) ferrocene palladium dichloride (1.80 g, 2.20mmol) and 1,4-dioxane ring (150ml), was heated at 85 and stirred for 24h.After completion of the reaction was allowed to cool, the reaction solution was extracted with ethyl acetate, washed with saturated brine three times, the resulting organic layer was dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate was removed under reduced pressure to remove the solvent.Separation by column chromatography, the mobile phase was chloroform / ethyl acetate = 6: 1.After the spin-dry vacuum dried to give a white powder product 12.0g, yield 97percent.
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 12h;Inert atmosphere;	<strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> (25.0 g, 107 mmol), bis(pinacolato)diboron (54.2 g, 214 mmol), Pd(dppf)2Cl2 (1.0 g, 10 mol percent), and potassium acetate (31.5 g, 321 mmol) were placed in 1 L round bottom flask. 600 mL of dioxane was then added to the flask. Nitrogen was bubbled into the reaction mixture for 1 h and then the flask was heated to 90° C. for 12 h in an atmosphere of nitrogen. The dioxane was removed under reduced pressure by a rotary evaporator. The dark solid was dissolved in 400 mL of dichloromethane and passed through a 2 inch thick silica gel plug. The dichloromethane was removed under reduced pressure by a rotary evaporator to leave a yellow oil. The product was then distilled using a Kuglerohr apparatus to give 23 g of a white solid (77percent yield).
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 90℃; for 3h;Inert atmosphere;	In a nitrogen flow, 11.72 g of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong>, 15.24 g of bispinacolatodiboron, 1.33 g of[PdCl2(dppf)]CH2Cl2, 14.14 g of potassium acetate, and 100 ml of dewatered dimethyl sulfoxide were put in a 200-mLfour-neck flask, and stirred in an oil bath at 90°C for 3 hours. Subsequently, this was cooled to room temperature, andwater and dichloromethane were added thereto for liquid separation washing, and thereafter the oily phase was driedwith sodium sulfate. Next, the solvent was removed under reduced pressure. The obtained residue was purified throughsilica gel column chromatography (eluent: ethyl acetate/hexane = 15/85) to give 14.70 g of a white solid (containing thecompound 1 and a starting material pinacolatodiboron as an impurity).

42.9 mg

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 100℃; for 2h;Inert atmosphere;

Under a nitrogen stream, 35.7 g of 2- (3-bromophenyl) pyridine, 42.6 g of bispinacolato diboron, 37.4 g of potassium acetate and 400 mL of dehydrated dimethylsulfoxide were charged, Nitrogen bubbling was carried out at 80 ° C. for 30 minutes while stirring. Thereto was added 22.50 g of [PdCl 2 (dppf)] CH 2 Cl, And the mixture was stirred in a 100 ° C. oil bath for 2 hours. Thereafter, the mixture was cooled to room temperature, water and toluene were added thereto, and the mixture was separated and washed, and the organic layer was dried with sodium sulfate. Then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate / hexane = 1/5) 42.9 g of Intermediate 6 was obtained as a white solid (containing pinacolato diboron raw material as impurity).

Reference： [1]Patent: CN103396355,2016,B .Location in patent: Paragraph 0059-0061
[2]Chemical Communications,2008,p. 889 - 890
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 15284 - 15288
Angew. Chem.,2015,vol. 127,p. 15499 - 15503,5
[4]Patent: US2015/307535,2015,A1 .Location in patent: Paragraph 0186
[5]Patent: EP2803671,2014,A1 .Location in patent: Paragraph 0251
[6]Patent: JP6119171,2017,B2 .Location in patent: Paragraph 0160; 0161

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 6 2-(3'-BrPh)Py 2-(3'-Bromophenyl)pyridine A mixture of 2-bromopyridine (2.40 g, 15.3 mmol), 3-bromophenylboronic acid (4.00 g, 19.9 mmol), tetrakis(triphenylphosphine) palladium (0) (1.24 g, 1.07 mmol), 2 M Na2CO3(aq) (16 cm3), EtOH (16 cm3) and toluene (44 cm3) was degassed and heated at reflux (with bath temperature 106° C.) under argon for 17 h. The reaction was allowed to cool to give an yellow orange mixture. The mixture was diluted with water (10 cm3) and ether (20 cm3). The two phases were separated. The aqueous layer was extracted with ether (3*15 cm3). The organic layer and the ether extracts were combined and dried over anhydrous sodium sulfate. The solvents were completely removed to leave an orange oil. The oil was purified by column chromatography over silica gel using ethyl acetate-light petroleum (0:1 to 1:10) as eluent to give 2.86 g (80percent) of 6 as a pale yellow oil; deltaH(200 MHz; CDCl3) 7.18-7.40 (2 H, m, PyH and ArH), 7.55 (1 H, m, ArH), 7.66-7.85 (2 H, m, PyH), 7.92 (1 H, m, ArH), 8.17-8.19 (1 H, m, ArH), and 8.71 (1 H, m, PyH). The 1H NMR is similar to the reported by M. van der Sluis, V. Beverwijk, A. Termaten, F. Bickelhaupt, H. Kooijman, A. L. Spek, Organometallics, 1999, 18, 1402-11407.

12
[ 4373-60-8 ]
[ 833485-13-5 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 58 - 63

13
[ 66943-05-3 ]
[ 4373-60-8 ]
[ 1239907-07-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 3958 - 3960

14
[ 109-04-6 ]
[ 591-18-4 ]
[ 4373-60-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		2-bromopyridine 6.0g (38.0 mmol) was dissolved in tetrahydrofuran, 300ml, was added to Tetrakistriphenylphosphine Pd (0) 2.2g (1.9 mmol) was stirred at room temperature for about 5 minutes. Thereafter, by the addition of 1-Bromo-3-iodobenzene 10.8g (38.0 mmol) of potassium carbonate and 10.5g (76.0 mmol). Then, when the mixture was heated under reflux for one day at 70 was added distilled water 150ml It turned on. When the reaction is complete, the extract was added to 100ml of ethyl acetate, and distilled under reduced pressure the organic layer was dried over magnesium sulfate. Purification by the results obtained from this by column chromatography to yield the intermediate 1-2 about 7.6g (32.3 mmol, 85percent yield). The resulting compound was confirmed by LC-MS.
		Reference Example 28; Preparation method of 2-(3-bromophenyl)pyridine; In the same manner as in Reference Example 25, except that a solution of tert-butyllithium in n-pentane was used instead of n-butyllithium, and 0.63 ml of 2-bromopyridine was used instead of 4-bromopyridine, 845 mg of the title compound was obtained. Physicochemical properties of this compound (1) Molecular formula: C11H8BrN (2) Mass spectrum (EI): m/z 233 (M)+ (3) 1H NMR spectrum (300 MHz, CDCl3) delta (ppm): 7.25 (ddd, pyridine), 7.33 (m, C6H4), 7.53 (ddd, C6H4), 7.69 (ddd, pyridine), 7.75 (ddd, pyridine), 7.90 (ddd, C6H4), 8.17 (dd, C6H4), 8.69 (ddd, pyridine).

Reference： [1]Patent: KR2016/6493,2016,A .Location in patent: Paragraph 0308; 0313; 0314; 0315
[2]Patent: EP1661904,2006,A1 .Location in patent: Page/Page column 45

15
[ 98-80-6 ]
[ 4373-60-8 ]
2-[(1,1′-biphenyl)-3-yl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 14h;Reflux; Inert atmosphere;	A sparged mixture of THF (45 mL) and H20 (5 mL) containing 0.69 g (3.0 mmol) of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong>38 and 400 mg (3.28 mmol) of phenylboronic acid was charged with 2.27 g (16.4 mmol) of K2C03 and 265 mg (0.229 mmol) ofPd(PPh3)4. The suspension was heated at reflux for 14 h under an inert atmosphere, then cooled and poured into H20. The product was extracted with diethyl ether, washed with brine, and then dried with MgS04. Filtration and removal of the solvent in vacuo resulted in an oil that was purified by column chromatography [basic Al203: DCM/hexane1 :1 ; Rf=0.78] affording 650 mg (95.2percent) of the product as a colorless oil. 1H NMR (400 MHz, CDCI3): delta=8.78 (ddd, 3J= 5 Hz, 4J=2 Hz, 5J=1 Hz, 1H,Ha), 8.32 (t, 4J=2 Hz, 1H, He), 8.03 (dt, 3J = 8 Hz, 4J = 2 Hz, 5J = 1 Hz, 1H, Hf), 7.85-7.67 (m, 5H, Hd, Hh, He, Hi), 7.59 (t, 3J=8 Hz, 1 H, Hg), 7.51 (t, 3J= 7 Hz, 2H,Hj), 7.42 (t, 3J=7 Hz, 1H, Hk), 7.28 (ddd, 3J=7 Hz, 4J = 5 Hz, 5J = 1 Hz, 1 H, Hb); 13C NMR (100 MHz, CDCI3): delta =157.1 , 149.4, 141.7, 140.9, 139.6, 136.9, 129.2, 128.8, 127.8, 127.4, 127.2, 125.8, 122.2, 120.6; HRMS (El): m/z = 231.1042 [(M)+] (calcd for C17H13N+: m/z = 231.1048).

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 4960 - 4971
[2]Patent: WO2012/155247,2012,A1 .Location in patent: Page/Page column 61-62
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 15284 - 15288
Angew. Chem.,2015,vol. 127,p. 15499 - 15503,5
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 11677 - 11680
Angew. Chem.,2015,vol. 127,p. 11843 - 11846,4

16
[ 109-04-6 ]
[ 859940-48-0 ]
[ 4373-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;	Synthesis Method Described in WO02/066552Under an inert gas atmosphere, 2-bromopyridine and 1.2 equivalents of 3-bromophenylboric acid were subjected to the Suzuki coupling (catalyst: tetrakis(triphenylphosphine)palladium(0), base: 2M sodium carbonate aqueous solution, solvent:ethanol, toluene), to obtain 2-(3'-bromophenyl)pyridine represented by the following formula:

Reference： [1]Patent: US2011/272686,2011,A1

17
[ 4373-60-8 ]
[ 1283748-32-2 ]

Reference： [1]Dyes and Pigments,2011,vol. 90,p. 139 - 145

18
[ 4373-60-8 ]
[ 1283748-33-3 ]

Reference： [1]Dyes and Pigments,2011,vol. 90,p. 139 - 145

19
[ 67492-50-6 ]
[ 4373-60-8 ]
[ 1395102-51-8 ]

Reference： [1]Organic electronics,2011,vol. 12,p. 2103 - 2110

20
[ 62-53-3 ]
[ 4373-60-8 ]
[ 1325592-74-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In xylene; for 6.33333h;Inert atmosphere; Reflux;	<strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> (4 g, 17.09 mmol), Pd2(dba)3 (0.156 g, 0.171 mmol), dicyclohexyl(2',6'-dimethoxy-[l,l'-biphenyl]-2- yl)phosphine (S-Phos) (0.281 g, 0.683 mmol), and sodium t-butoxide (2.463 g, 25.6 mmol) were mixed in 100 mL of xylene. The solution was bubbled with nitrogen for 20 min. Aniline (2.387 g, 25.6 mmol) was added. The reaction was heated up to reflux for 6 h. After cooled to rt, dichloromethane was added. The mixture was filtered through Celite.(R).. The solvent was then evaporated. The residue was coated on Celite.(R). and columned with 1 :5 hexanes/ethyl acetate to give N-phenyl-3-(pyridin-2-yl)aniline (3.6 g, 14.62 mmol, 86 percent yield) as light yellow solid.
75%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux;	23.4 g (100 mmol) of <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong>, 9.3 g (100 mmol) of aniline, 2.87 g (5.0 mmol) of bis(dibenzylideneacetone)palladium(0) (Pd(dba)2), 2.0 g (10 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 14.4 g (150 mmol) of sodium tert-butoxide (NaOtBu) were added to a flask, 200 mL of toluene was added thereto, and the flask was purged with nitrogen. The resultant mixture was refluxed for 24 hours, cooled to room temperature, and extracted by using dichloromethane/water (MC/H2O). The organic layer was dried by using magnesium sulfate (MgSO4) and concentrated. The crude product was purified by column chromatography (hexane/ethyl acetate=3/1) to obtain Intermediate 1-2 (yield=75percent).

Reference： [1]Patent: WO2012/116231,2012,A2 .Location in patent: Page/Page column 140
[2]Patent: US2018/309072,2018,A1 .Location in patent: Paragraph 0309; 0314; 0315

21
[ 4373-60-8 ]
[ 1395093-42-1 ]

Reference： [1]Patent: WO2012/116231,2012,A2

22
[ 4373-60-8 ]
C₃₈H₃₄N₄Pt [ No CAS ]

Reference： [1]Patent: WO2012/116231,2012,A2

23
[ 4373-60-8 ]
[ 1228825-80-6 ]

Reference： [1]Patent: WO2012/155247,2012,A1

24
[ 4373-60-8 ]
[ 1228825-81-7 ]

Reference： [1]Patent: WO2012/155247,2012,A1

25
[ 28035-71-4 ]
[ 4373-60-8 ]
C₂₈H₂₁BrN₂O₂S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 8995 - 9000
Angew. Chem.,2013,vol. 125,p. 9165 - 9170,6

26
[ 108-36-1 ]
[ 81745-83-7 ]
[ 136538-84-6 ]
[ 4373-60-8 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12356 - 12375

27
[ 109-04-6 ]
[ 136538-84-6 ]
[ 4373-60-8 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12356 - 12375

28
[ 4373-60-8 ]
2-(5-bromo-2-nitrophenyl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 11862 - 11866
Angew. Chem.,2013,vol. 125,p. 12078 - 12082,5

29
[ 4373-60-8 ]
2-(2-azido-5-bromophenyl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 11862 - 11866
Angew. Chem.,2013,vol. 125,p. 12078 - 12082,5
[2]RSC Advances,2015,vol. 5,p. 100223 - 100227
[3]Journal of Organic Chemistry,2016,vol. 81,p. 8142 - 8154

30
[ 13154-24-0 ]
[ 4373-60-8 ]
[ 1533455-03-6 ]

Yield	Reaction Conditions	Operation in experiment
43.3%		Synthesis of 2-(3-(tri-isopropylsilyl)phenyl)pyridine 2-(3-Bromophenyl)pyridine (7.46 g, 31.9 mmol) was dissolved in THF (300 mL) in a 500 mL 3-neck round bottom flask. The system was evacuated and filled with nitrogen three times then maintained under nitrogen. The flask was placed in a dry ice/acetone bath and cooled to below -60° C. 2.5 M n-butyllithium (14.0 mL, 35.1 mmol) was added. The solution went from pale yellow to a dark green solution. After one hour, chlorotriisopropylsilane (10.91 mL, 51.0 mmol) was added via syringe in portions while keeping the reaction temperature below -60° C. before removal of the ice bath. The reaction was allowed to warm up to ambient temperature. After three hours, the reaction mixture was quenched with water then partitioned between brine and ethyl acetate. The aqueous portion was extracted with ethyl acetate two times. The combined organic layers were washed once with brine solution, dried over sodium sulfate, filtered and evaporated to produce an orange oil. The crude product was adsorbed onto Celite® and purified with chromatography using a mobile phase of 1-5percent ethyl acetate in hexane to give (4.3 g, 43.3percent) of the title compound as yellow oil.

Reference： [1]Patent: US2014/8617,2014,A1 .Location in patent: Paragraph 0161; 0162

31
[ 144-79-6 ]
[ 4373-60-8 ]
[ 1533455-10-5 ]

Yield	Reaction Conditions	Operation in experiment
69%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃; for 18h;	Synthesis of 2-(3-(methyldiphenylsilyl)phenyl)pyridine 2-(3-Bromophenyl)pyridine (3 g, 12.82 mmol) was added to dry THF (250 mL) and was cooled to -78° C. Chloro(methyl)diphenylsilane (4.24 mL, 19.22 mmol) was added drop wise to the solution and allowed to stir to room temperature for 18 hours. The reaction mixture was quenched with saturated ammonium chloride solution. The crude product was partitioned between brine and ethyl acetate. Organic layers were combined, dried and solvents were removed under reduced pressure. The isolated product was purified by silica gel column chromatography using 1-5percent ethyl acetate/hexanes as eluent. The isolated material was further purified by distillation to give 2-(3-(methyldiphenylsilyl)phenyl)pyridine (3.9 g, 69percent).

Reference： [1]Patent: US2014/8617,2014,A1 .Location in patent: Paragraph 0183; 0184

32
[ 4373-60-8 ]
[ 1533455-04-7 ]

Reference： [1]Patent: US2014/8617,2014,A1

33
[ 4373-60-8 ]
[ 1533454-64-6 ]

Reference： [1]Patent: US2014/8617,2014,A1

34
[ 4373-60-8 ]
[ 1533454-65-7 ]

Reference： [1]Patent: US2014/8617,2014,A1

35
[ 76-86-8 ]
[ 4373-60-8 ]
[ 1533455-09-2 ]

Yield	Reaction Conditions	Operation in experiment
78%		Preparation of 2-(3-(triphenylsilyl)phenyl)pyridine <strong>[4373-60-8]2-(3-bromophenyl)pyridine</strong> (5 g, 21.36 mmol) was dissolved in THF (214 mL) and cooled to -78° C. n-Butyl lithium (2.5M solution in hexanes, 9.40 mL, 23.50 mmol) was slowly added to the cooled reaction mixture and this was stirred for another 30 minutes in cold bath after complete addition. Chlorotriphenylsilane (7.56 g, 25.6 mmol) dissolved in THF (30 mL) was slowly added to the reaction mixture which was then allowed to come to room temperature and stirred for another 18 h. The reaction mixture was quenched with saturated NH4Cl solution. The reaction mixture was partitioned between brine and ethyl acetate. The organic layers were combined, dried over MgSO4 and solvents were removed under reduced pressure. The off-white crude product was purified by column chromatography over silica gel using 2-8percent ethyl acetate/hexanes as eluent. The isolated oily material was recrystallized from hexanes/DCM to obtain 2-(3-(triphenylsilyl)phenyl)pyridine (6.91 g, 78percent) as a white crystalline solid.

Reference： [1]Patent: US2014/8617,2014,A1 .Location in patent: Paragraph 0179; 0180

36
[ 4373-60-8 ]
[ 1245636-12-7 ]
[ 1565863-81-1 ]
[ 1565863-80-0 ]

Reference： [1]ChemCatChem,2014,vol. 6,p. 123 - 126

37
[ 4373-60-8 ]
[ 1565863-79-7 ]

Reference： [1]ChemCatChem,2014,vol. 6,p. 123 - 126

38
[ 4373-60-8 ]
[ 1565863-79-7 ]
[ 1565863-78-6 ]
[ 1565863-77-5 ]

Reference： [1]ChemCatChem,2014,vol. 6,p. 123 - 126

39
[ 4373-60-8 ]
[ 1565863-81-1 ]

Reference： [1]ChemCatChem,2014,vol. 6,p. 123 - 126

40
[ 4373-60-8 ]
N,N-di(3-(pyridin-2-yl)phenyl)aniline [ No CAS ]

Reference： [1]Patent: WO2014/15936,2014,A1

41
[ 4373-60-8 ]
N,N-bis[3-(pyridin-2-yl)phenyl]mesitylamine [ No CAS ]

Reference： [1]Patent: WO2014/15936,2014,A1

42
[ 4373-60-8 ]
N,N-bis[3-(pyridin-2-yl)phenyl]4-(9H-carbazole-9-yl)aniline [ No CAS ]

Reference： [1]Patent: WO2014/15936,2014,A1

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[ CAS No. 4373-60-8 ]

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[ 4373-60-8 ] Synthesis Path-Upstream 1~2

[ 4373-60-8 ] Synthesis Path-Downstream 1~42

Related Functional Groups of [ 4373-60-8 ]

Bromides

Aryls

Related Parent Nucleus of [ 4373-60-8 ]

Pyridines

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[ 4373-60-8 ]

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[ 4373-60-8 ]