Sodium 3-chlorobenzene-1-sulfinate → tert-butyl 8-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

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Reaction Steps

The product of Example 29, step B (230 mg, 0.65 mmol) and sodium 3-chlorobenzenesulfinate (155 mg, 0.78 mmol) were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate) provided tert-butyl 8-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (78 mg, 26%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.08 (s, 1H), 7.93 (t, J=1.8 Hz, 1H), 7.86-7.83 (m, 1H), 7.83-7.81 (m, 1H), 7.56-7.48 (m, 2H), 7.43 (t, J=7.8 Hz, 1H), 4.58 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.91-2.84 (m, 2H), 1.51 (s, 9H).

Provenance & Evidence