[ CAS No. 3510-66-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 3510-66-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3510-66-5 ]

SDS Specification

Alternatived Products of [ 3510-66-5 ]

Product Details of [ 3510-66-5 ]

CAS No. :	3510-66-5	MDL No. :	MFCD00209553
Formula :	C₆H₆BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YWNJQQNBJQUKME-UHFFFAOYSA-N
M.W :	172.02	Pubchem ID :	564216
Synonyms :

Calculated chemistry of [ 3510-66-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.9
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.12

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.186 mg/ml ; 0.00108 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	0.858 mg/ml ; 0.00499 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.0948 mg/ml ; 0.000551 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 3510-66-5 ]

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 [ 3510-66-5 ]

* 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 [ 3510-66-5 ]
Downstream synthetic route of [ 3510-66-5 ]

[ 3510-66-5 ] Synthesis Path-Upstream 1~4

1
[ 3510-66-5 ]
[ 38203-08-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; acetonitrile	Step 3-Preparation of 2-(5-methylpyridin-2-yl)acetonitrile To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO₄, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent). ¹H NMR (300 MHz, CDCl₃): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J₁=3.0 Hz, J₂=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).

Reference： [1] Patent: US2009/280230, 2009, A1,
[2] Patent: US2009/280230, 2009, A1,
[3] Patent: US2009/280230, 2009, A1,

2
[ 3510-66-5 ]
[ 75-05-8 ]
[ 38203-08-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere Stage #2: at -78 - 20℃; for 2 h;	To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO₄, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent). ¹H NMR (300 MHz, CDCl₃): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J₁=3.0 Hz, J₂=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).

Reference： [1] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 79
[2] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 73

3
[ 3510-66-5 ]
[ 77152-08-0 ]
[ 1620-71-9 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11126 - 11146

4
[ 3510-66-5 ]
[ 308846-06-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1017 - 1022
[3] Patent: WO2011/20615, 2011, A1,
[4] Patent: EP2289883, 2011, A1,
[5] Patent: WO2012/128582, 2012, A2,

[ 3510-66-5 ] Synthesis Path-Downstream 1~13

1
[ 3510-66-5 ]
[ 4434-13-3 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 1932,1934

2
[ 3510-66-5 ]
[ 101990-45-8 ]
[ 154321-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In dichloromethane; water; for 0.5h;Heating / reflux;	Generally, to a refluxing mixture of 2-bromo-methyl-pyridine (5 g, 29 mmol) in a biphasic medium of DCM (500 ml) and water (500 ml) was added Br2 (1.65 ml, 31.9 mmol). The mixture was illuminated using a halogen lamp (500 W, distance: 5-10 cm) under reflux for 30 min. The solution was cooled to room temperature and neutralized with a 10% Na2CO3 aqueous solution and solid NaCl was added. The aqueous layer was extracted three times with DCM, the combined organic extracts were dried over MgSO4 and evaporated in vacuo. HPLC analysis of the crude product showed the relative ratio of 13.6:76.5:9.9 (Retention time: 8.1, 10.6 and 13.4 min, respectively) for starting material 2-bromo-methyl-pyridine:2-bromo-5-(bromomethyl)pyridine: 2-bromo-5-(dibromomethyl)pyridine.

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 1697 - 1700
[2]Tetrahedron Letters,2002,vol. 43,p. 1697 - 1700
[3]Synthesis,1994,p. 87 - 92
[4]Patent: US2007/219276,2007,A1 .Location in patent: Page/Page column 41

3
[ 3510-66-5 ]
[ 64-17-5 ]
[ 201230-82-2 ]
[ 55876-82-9 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4494 - 4506

4
[ 3510-66-5 ]
2-bromo-5-tribromomethyl-pyridine [ No CAS ]
[ 101990-45-8 ]
[ 154321-32-1 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3845 - 3848

5
[ 3510-66-5 ]
[ 957061-12-0 ]
[ 1000587-40-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,1-dimethoxyethylene; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.
56%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic Acid Methyl Ester; To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.
56%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.

40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester; EPO <DP n="58"/>To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5ml/ ImI) was added 3-nitro-5- (4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 1300C for 0.5 h. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2ZMeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic Acid Methyl Ester; To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave heating;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate; In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave radiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl esterTo a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).

Reference： [1]Patent: US2008/4442,2008,A1 .Location in patent: Page/Page column 194
[2]Patent: US2009/163502,2009,A1 .Location in patent: Page/Page column 37-38
[3]Patent: US2015/191487,2015,A1 .Location in patent: Paragraph 0626
[4]Patent: WO2008/55840,2008,A1 .Location in patent: Page/Page column 56-57
[5]Patent: US2009/163499,2009,A1 .Location in patent: Page/Page column 32
[6]Patent: US2009/170873,2009,A1 .Location in patent: Page/Page column 47
[7]Patent: US2009/170874,2009,A1 .Location in patent: Page/Page column 62-63
[8]Patent: US2010/152203,2010,A1 .Location in patent: Page/Page column 23
[9]Patent: US2012/22067,2012,A1 .Location in patent: Page/Page column 36
[10]Patent: US2010/324069,2010,A1 .Location in patent: Page/Page column 27
[11]Patent: US2010/324056,2010,A1 .Location in patent: Page/Page column 33-34

6
[ 3510-66-5 ]
[ 128-08-5 ]
[ 101990-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dibenzoyl peroxide; In chloroform; for 6h;Heating / reflux;	Step 2: 2-Bromo-5-bromomethylpyridine To a suspension of 2-bromo-5-methylpyridine (170g, 0. [95MO1)] in [CC14] (2L) was added NBS (193g, [1.] [08MOL)] and benzoylperoxide (15g) and the mixture was refluxed for 6h. The reaction mixture was cooled down to rt and the solid formed was filtered off. The filtrate was concentrated affording 275g of crude 2-bromo-5-bromomethylpyridine which was used without further purification in the next step (mixture of mono-bromo and di-bromo). [TLC, [RF=] 0.7, pet. ether/ethylacetate 9: 1].

Reference： [1]Patent: WO2003/106455,2003,A1 .Location in patent: Page 55

7
[ 3510-66-5 ]
[ 151169-74-3 ]
[ 847406-05-7 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 90℃; for 48h;	To a stirred solution of 2-bromo-5-methyl- pyridine (1.00 g, 5.81 mmol) and 2,3-dichloro phen- ylboronic acid (1.33 g, 6. 98 mmol) in DME (5.8 ML) was added potassium carbonate (1.21 g, 8.7 mmol). The mixture was degassed by bubbling nitrogen with a syringe for 5 min through the mixture, followed by addition of Pd (PPH3) 4 (0.672 g, 0.58 MMOL). A reflux condenser was attached to the flask and the mixture heated to 90C FOR 48 h. The mixture was cooled to ambient temperature and partitioned between. ethyl acetate and brine. The organic phase was washed with brine (3X20 mL) and dried over sodium sulfate, filtered, and concentrated IN VACUO. The resulting oil was purified by flash chromatography on silica gel ELUTING WITH 1 : 1 ethyl acetate: hexane to provide the title compound' (0. 380 g, 5. 81. MMOL, 27% yield) as A light yellow oil which ch solidified upon standing to an off with solid. 1H NMR (CDCl3, 400 MHz) 5 8. 54 (M, 1H), 7. 58 (m, 1H), 7.5 (s, 2H), 7.44 (DD, J=1.56, 7.42 Hz, 1H), 7.43 (m, 1H), 7. 27 (t, J=7.81 Hz, 1H), 2. 40 (s, 3H).

Reference： [1]Patent: WO2005/19200,2005,A2 .Location in patent: Page/Page column 97-98

8
[ 3510-66-5 ]
[ 4214-79-3 ]
[ 210037-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	With K2CO3; copper; In dichloromethane;	Step 1 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96(d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65(dd, J=2.4 and 8.2 Hz, 1H), 7.32(dd, J=2.9 and 9.7 Hz, 1H), 6.61(d, J=9.7 Hz, 1H) and 2.39(s,3H)ppm.
	With copper; potassium carbonate; In dichloromethane;	Step A Preparation of 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96(d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65 (dd, J=2.4 and 8.2 Hz, 1H), 7.32 (dd, J=2.9 and 9.7 Hz, 1H), 6.61 (d, J=9.7 Hz, 1H) and 2.39 (s, 3H)ppm.
	With copper; potassium carbonate; at 180℃; for 16h;	Step 1: 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96 (d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65 (dd, J=2.4 and 8.2 Hz, 1H), 7.32 (dd, J=2.9 and 9.7 Hz, 1H), 6.61 (d, J=9.7 Hz, 1H) and 2.39 (s, 3H) ppm.

Reference： [1]Patent: US2003/220241,2003,A1
[2]Patent: US6297239,2001,B1
[3]Patent: US2005/137207,2005,A1 .Location in patent: Page/Page column 99

9
[ 3510-66-5 ]
[ 75-09-2 ]
[ 4214-79-3 ]
[ 584-08-7 ]
[ 210037-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper;	Step 1 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2 CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2 Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1 H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96(d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65(dd, J=2.4 and 8.2 Hz, 1H), 7.32(dd, J=2.9 and 9.7 Hz, 1H), 6.61(d, J=9.7 Hz, 1H) and 2.39(s,3H)ppm.

Reference： [1]Patent: US5939439,1999,A

10
[ 3510-66-5 ]
[ 13598-45-3 ]
[ 110-18-9 ]
[ 7446-09-5 ]
[ 65938-77-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sec.-butyllithium; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; cyclohexane; water;	PREPARATION 4 5-Methyl-2-pyridinesulfonamide STR142 Sec-butyllithium (9.8 ml of 1.3 M in cyclohexane) and N,N,N'N'-tetramethylethylenediamine (1.8 ml, 12.2 mmol) were added to a stirred solution of 2-bromo-5-methylpyridine (2 g, 11.6 mmol) at -78 C. under a nitrogen atmosphere. After 90 min sulphur dioxide (approximately 30 ml) was condensed into the reaction mixture using a cold finger and the reaction mixture was slowly warmed to room temperature over 12 h. The reaction mixture was concentrated to dryness and the residue dissolved in ice-water. To this was added a mixture of sodium hydroxide (1.39 g, 35 mmol) and hydroxylamine sulphonic acid (3.9 g, 35 mmol) in water (20 ml). After 24 h the solution was extracted with ethyl acetate, dried (MgSO4) and concentrated. Flash column chromatography (95% dichloromethane/5% methanol) gave the product (250 mg) as a clear oil which crystallized on standing. 1 H NMR (400 MHz, CDCl3): delta=2.40 (s, 3 H), 5.20 (brs, 2 H), 7.80 (d, 1 H), 7.90 (d, 1 H), 8.50 (s, 1 H). LRMS (Thermospray): 172.8 (MH+).

Reference： [1]Patent: US6017945,2000,A

11
[ 3510-66-5 ]
[ 15016-42-9 ]
5-methyl-2-(2-vinylphenyl)pyridine [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 9114 - 9118

12
[ 3510-66-5 ]
[ 15016-42-9 ]
3,7-dimethyl-6H-pyrido[2,1-a]isoquinolin-6-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 9114 - 9118

13
[ 4434-13-3 ]
[ 3510-66-5 ]

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

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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[ 3510-66-5 ]

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[ 3510-66-5 ]

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[ CAS No. 3510-66-5 ] {[proInfo.proName]}

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[ 3510-66-5 ] Synthesis Path-Upstream 1~4

[ 3510-66-5 ] Synthesis Path-Downstream 1~13

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Bromides

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Pyridines

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[ 3510-66-5 ]

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[ 3510-66-5 ]