Sodium Methoxide → 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methylphenyl)quinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A pressure tube was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-fluoro-2-methylphenyl)amino)phenyl)acrylate (3.19 g, 6.37 mmol) and MeOH (31.9 ml) to give a yellow suspension. Sodium methoxide (25 wt % in MeOH) (0.697 ml, 2.55 mmol) was added. The tube was sealed and heated to 70° C. for 18 h. The whole was cooled to rt, quenched with saturated aq NH4Cl, and concentrated. The whole was extracted with EtOAc (3×50-mL). The organic layer was separated, combined, dried over MgSO4, filtered, and concentrated to afford orange residue. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 20% EtOAc in heptane, to provide 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methylphenyl)quinolin-2(1H)-one (2.45 g, 85% yield) as yellow solid. m/z (ESI) [M+H]+=454.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (s, 3 H) 3.36 (s, 2 H) 5.74 (d, J=8.80 Hz, 1H) 5.93 (d, J=9.59 Hz, 1 H) 6.34-6.50 (m, 6 H) 6.62 (dd, J=8.85, 2.10 Hz, 1 H) 6.89 (d, J=2.05 Hz, 1 H) 6.99 (m, 1 H) 7.16 (d, J=9.39 Hz, 1 H).

Provenance & Evidence