Sodium Methoxide → 6-(benzylthio)-1-(4-bromo-2-methoxyphenyl)quinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino) phenyl)acrylate (86.95 g, 174 mmol) in 350 mL MeOH was heated to 70° C., was treated with sodium methoxide 25% wt in MeOH (19.06 ml, 69.8 mmol) and was allowed to stir overnight. The reaction mixture was then concentrated. The crude solid was triturated with IPA yielding 47.13 g clean product. The IPA washings were concentrated. Purification of the crude residue by silica gel column chromatography (0-100% EtOAc/heptane) gave an additional 10.76 g of slightly impure product. 6-(benzylthio)-1-(4-bromo-2-methoxyphenyl)quinolin-2(1H)-one (57.89 g, 128 mmol, 73.4% yield). (ESI) 451.8 (M+H)+.

Provenance & Evidence