Trifluoroacetic acid → 8-(4-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine

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Reaction Steps

To the product obtained in step A (150 mg, 0.31 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (0.6 mL). After stirring for 2 h at ambient temperature the reaction mixture was quenched with 10% sodium bicarbonate solution (20 mL) and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 90:10 dichloromethane/methanol) to give 8-(4-fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (60 mg, 52%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.03 (d, J=1.8 Hz, 1H), 8.00-7.92 (m, 2H), 7.78 (dd, J=8.7, 2.1 Hz, 1H), 7.51 (d, J=9.0 Hz, 1H), 7.21-7.10 (m, 2H), 4.00 (t, J=2.1 Hz, 2H), 3.25 (t, J=5.7 Hz, 2H), 2.84-2.76 (m, 2H).

Provenance & Evidence