Sodium Methoxide → HCID 117736910, compound

Participants

Reaction Conditions

Reaction Steps

A 25-mL pressure vessel was charged with (E)-ethyl 3-(5-(benzylthio)-2-((3-(3-fluorophenyl)cyclopentyl)amino)phenyl)acrylate (800 mg, 1.682 mmol), methanol (8.4 ml), and a solution of sodium methoxide in methanol (0.5 M, 3.4 mL, 1.682 mmol). The reaction. vessel was sealed with a Teflon cap and the yellow reaction mixture was warmed to 100° C. After 36 h, additional solution of sodium methoxide in methanol (0.5 M, 3.4 mL, 1.682 mmol) was added and the reaction vessel was sealed and warmed to 100° C. After 12 h, the reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure to furnish a yellow residue, which was purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 30% EtOAc in heptane) to afford 6-(benzylthio)-1-(3-(3-fluorophenyl)cyclopentyl)quinolin-2(1H)-one (170 mg, 0.396 mmol, 23.53% yield). m/z (ESI) 430.1 (M+H)+.

Provenance & Evidence