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

Participants

Reaction Steps

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate (3.13 g, 6.28 mmol) and MeOH (31.4 ml) to give a yellow suspension. Sodium methoxide (25 wt % in MeOH) (0.271 ml, 1.256 mmol) was added. A reflux condenser was attached, and the flask was lowered into a 75° C. heating bath. The bath quickly spiked to ca. 80-85° C., but returned to 70-75° C. after 30 min. The reaction was stirred for 16 hrs, and the mixture was diluted with DCM and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel loading column, 10-60% EtOAc/Heptane) to give 6-(benzylthio)-1-(4-bromo-2-methoxyphenyl)quinolin-2(1 H)-one (1.95 g, 4.31 mmol, 68.6% yield) as a yellow solid. 1 H NMR (400 MHz, DMSO-d6) □=7.94 (d, J=9.5 Hz, 1 H), 7.78 (d, J=2.2 Hz, 1 H), 7.50 (d, J=2.1 Hz, 1 H), 7.43-7.16 (m, 8 H), 6.66 (d, J=9.6 Hz, 1 H), 6.47 (d, J=8.8 Hz, 1 H), 4.23 (s, 2 H), 3.69 (s, 3 H). m/z (ESI) 452.0 (M+H)+.

Provenance & Evidence