Dimethyl Sulfate → tert-butyl 6-methoxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Participants

Reaction Steps

To a solution of the product of step A (470 mg, 1.06 mmol) in acetone (45 mL) under a nitrogen atmosphere was added potassium carbonate (1.34 g, 9.7 mmol) and dimethylsulfate (0.22 mL, 2.11 mmol). The reaction mixture was refluxed for 2 h, cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2, 8:2, hexanes/ethyl acetate) to provide tert-butyl 6-methoxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (400 mg, 82%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.96-7.94 (m, 2H), 7.71 (br s, 1H), 7.58-7.48 (m, 3H), 7.33 (s, 1H), 4.55 (s, 2H), 4.04 (s, 3H), 3.82 (br s, 2H), 2.87 (br s, 2H), 1.50 (s, 9H).

Provenance & Evidence