Sodium Carbonate → 4-Chloro-2-(2,5-difluorophenyl)-7-fluoro-3-methylquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 2,4-dichloro-7-fluoro-3-methylquinoline (300 mg, 1.30 mmol) (in a mixture with the 5-F regioisomer; described herein), 2,5-difluorophenylboronic acid (268 mg, 1.70 mmol), tetrakis(triphenylphosphine)palladium(o) (151 mg, 0.130 mmol), and sodium carbonate (69 mg, 6.52 mmol) in acetonitrile (9.7 mL) and water (4.9 mL) was stirred and heated in a microwave at 100° C. for 120 min. The reaction mixture was then partitioned between EtOAc and water, and the organic layer was washed with brine, dried (MgSO4), and concentrated. Column chromatography of the crude product afforded 4-chloro-2-(2,5-difluorophenyl)-7-fluoro-3-methylquinoline) as a white solid. Mass Spectrum (ESI) m/e=308 (M+1).

Provenance & Evidence