5-Methyl-2-(tri-n-butylstannyl)pyridine → 4-Chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-2-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.6 g, 2.419 mmol) in toluene (4.84 mL) was added 5-methyl-2-(tributylstannyl)pyridine (1.02 g, 2.66 mmol), and palladium tetrakistriphenylphosphine (0.280 g, 0.24 mmol). The reaction was stirred at 100° C. and stirring continued for 42 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-(5-methyl-2-pyridinyl)-quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

Provenance & Evidence