Acetonitrile → 4-Chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dichloro-7-fluoro-3-methylquinoline (100 mg, 0.44 mmol), 2-(methylthio)phenylboronic acid (95 mg, 0.57 mmol) (in a mixture with the 5-F regioisomer; described herein), tetrakis(triphenylphosphine)palladium(o) (25.1 mg, 0.022 mmol), sodium carbonate (230 mg, 2.17 mmol), acetonitrile (3 mL), and water (1.5 mL) was heated in a microwave at 100° C. for 60 min, then partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), and concentrated. Column chromatography afforded (in order of elution) 4-chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline and 4-chloro-5-fluoro-3-methyl-2-(2-(methylthio)phenyl) as white solids. Mass Spectrum (ESI) m/e=318 (M+1).

Provenance & Evidence