2-(Tributylstannyl)pyridine → 4,8-Dichloro-3-methyl-2-(pyridin-2-yl)quinoline

HRID 1431338Notes

Reaction equation

HRID 1431338 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 596312172,4,8-Trichloro-3-methylquinoline

Product 1

HCID 596310354,8-Dichloro-3-methyl-2-(pyridin-2-yl)quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The dichloride was prepared according to Procedure E using 2,4,8-trichloro-3-methylquinoline (0.475 g, 1.927 mmol), 2-(tributylstannyl)pyridine (0.780 mL, 2.120 mmol), palladium tetrakistriphenylphosphine (0.223 g, 0.193 mmol) in toluene (3.85 mL) to give 4,8-dichloro-3-methyl-2-(pyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=289.0 (M+1).

Sources & evidence

ORD record
ord-d6e6a1aa80de42d5a150a9a0d857fa29
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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