Methanol → HCID 117737033, compound

Participants

Reaction Conditions

Reaction Steps

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-cyano-2-methoxyphenyl)amino)phenyl)acrylate (963 mg, 1.840 mmol) and MeOH (9199 μl) to give a thick, yellow suspension. Sodium methoxide (25 wt % in MeOH) (80 μl, 0.368 mmol) was added. A reflux condenser was attached, and the flask was heated to 80° C. overnight. In the morning, the mixture was diluted with DCM and concentrated. The residue was taken up in 2-PrOH, heated briefly to boiling, then sonicated for 20 s. The mixture was cooled then filtered. The collected solid was washed with 2-PrOH, then dried under a stream of N2 (g). The filtration was repeated with the filtrate. The two lots of material were combined to give 5-(6-(benzylthio)-2-oxoquinolin-1(2H)-yl)-2-bromo-4-methoxybenzonitrile (798 mg, 1.672 mmol, 91% yield) as a light-orange solid. m/z (ESI) 477.0 (M+H)+.

Provenance & Evidence