2-Methyl-6-(tributylstannyl)pyridine → 4-Chloro-5,7-difluoro-3-methyl-2-(6-methylpyridin-2-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.2 g, 0.806 mmol) in toluene (1.60 mL) was added 2-methyl-6-(tributylstannyl)pyridine (0.34 g, 0.89 mmol), and palladium tetrakistriphenylphosphine (0.093 g, 0.081 mmol). The reaction was stirred at 100° C. and stirring continued for 18 h. The reaction mixture was cooled to rt and concentrated in vacuo. The crude material was purified by column chromatography on silica gel, eluting with (0-50% EtOAc in hexanes) to provide 4-chloro-5,7-difluoro-3-methyl-2-(6-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

Provenance & Evidence