Formic Acid → HCID 22676775, compound

Participants

Reaction Steps

Formic acid (4 mL) was added dropwise to a stirred solution of tert-Butyl 3-[3-(cyclopropylmethoxy)phenyl]-1-[(4-fluorophenyl)methyl]indole-2-carboxylate (Example 72, 431 mg, 0.91 mmol) in dichloromethane (1.0 mL). The reaction was stirred at room temperature for 8 h, then concentrated in vacuo. The resulting solids were placed on a pad of silica gel and purified by chromatography (gradient from 30% ethyl acetate/hexane to 100% ethyl acetate) to afford 3-[3-(cyclopropylmethoxy)phenyl]-1-[(4-fluorophenyl)methyl]indole-2-carboxylic acid (324 mg, 85%): mp=200-202° C., 1H NMR acetone-d6) 0.32-0.37 (m, 2 H), 0.55-0.61 (m, 2 H), 1.21-1.31 (m, 1 H), 3.86 (d, J=7.0 Hz, 2 H), 5.90 (s, 2 H), 6.89-6.93 (m, 1 H), 7.00-7.08 (m, 4 H), 7.11-7.16 (m, 2 H), 7.18-7.24 (m, 2 H), 7.30-7.36 (m, 2 H), 7.52-7.58 (m, 2 H), 11.28 (br s, 1 H); mass spectroscopy gave MH+=416 (60%).

Provenance & Evidence