Dimethyl Sulfate → HCID 22253350, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 1-(1-Ethyl-propyl)-6-methyl-4-(2,4,6-trimethyl-phenoxy)-1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one (134 mg, 0.381 mmol) in 2 ml of HMPA was added 60% sodium hydride in oil (20 mg, 0.5 mmol) and the resulting mixture was stirred at 0° C. for 10 min. Dimethyl sulfate (66.5 mg, 0.53 mmol) was added and stirred for 30 min. The reaction mixture was quenched with dilute acid to pH4 and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give a clear oil. The oil was purified through silica gel column chromatography using 3% ethyl acetate in hexane as eluent to give 70 mg of the title compound as white solid. 1H NMR (CDCl3) δ 6.88(s,2H), 6.61(s,1H), 4.0(m,1H), 3.95(s,3H), 2,44(s,3H), 2.29(s,3H), 2.26(s,3H), 2.10(s,6H), 1.95–2.1(m,2H), 1.7–1.9(m,2H), 0.78(t,6H)ppm.

Provenance & Evidence