m-Chloroperbenzoic acid → tert-butyl 6-chloro-8-(phenylsulfinyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

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Reaction Steps

To a solution of the product of Example 91, step A (50 mg, 0.12 mmol) in dichloromethane (2.0 mL) at −10° C. was added a solution of m-chloroperoxybenzoic acid (18 mg, 0.108 mmol) in dichloromethane (1.0 mL) drop wise. The reaction mixture was stirred at ambient temperature for 2 h, concentrated in vacuo and purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate) providing tert-butyl 6-chloro-8-(phenylsulfinyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (30 mg, 58%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.68-7.63 (m, 3H), 7.51-7.45 (m, 4H), 4.55 (s, 2H), 3.86-3.77 (m, 2H), 2.93-2.85 (m, 2H), 1.50 (s, 9H).

Provenance & Evidence