Hydrochloric Acid → HCID 68108369, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of step B (65 mg, 0.10 mmol), 1,1,3,3-tetramethoxypropane (18 μL, 0.11 mmol) and concentrated HCl (0.25 mL) was dissolved in ethanol (5 mL). The reaction flask was purged with argon, sealed and heated at 100° C. for 5 h. The reaction mixture was cooled to ambient temperature, quenched with 10% sodium bicarbonate solution, and extracted with dichloromethane. The organic extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 93:7 dichloromethane/methanol) to give 8-(phenylsulfonyl)-6-(1H-pyrazol-1-yl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (23 mg, 56%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.48 (dd, J=2.8, 0.4 Hz, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.03-7.97 (m, 2H), 7.93 (d, J=1.6 Hz, 1H), 7.82-7.77 (m, 1H), 7.58-7.45 (m, 3H), 6.53 (dd, J=2.4, 2.0 Hz, 1H), 4.01 (t, J=2.0 Hz, 2H), 3.27 (t, J=5.6 Hz, 2H), 2.90-2.81 (m, 2H).

Provenance & Evidence