HCID 22638712, compound → HCID 22638753, compound

Participants

Reaction Steps

Butyl lithium (1.4 ml of 2.4M in hexane, 3.36 mmol) was added drop wise over a five min period under a nitrogen atmosphere to a stirred solution of methyltriphenylphosphonium bromide (1.186 g, 3.32 mmol) in dry THF (25 ml). The solution was stirred for 30 min at ambient temperature and then added dropwise to a solution of 3-(2-formyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (1.10 g, 3.018 mmol) in 25 ml THF. The mixture was stirred for 24 hr, and then quenched with saturated aqueous ammonium acetate (2 ml). The mixture was concentrated in vacuo and then extracted with ethyl acetate (20 ml). The ethyl acetate extract was washed with water (10 ml), then washed with brine (10 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel using methylene chloride as the eluent to give 1-(toluene-4-sulfonyl)-3-(2-vinyl-cyclopropyl)-1H-indole-5-carbonitrile (755 mg, 71%). 1H NMR (300 MHz, CDCl3): δ8.04 (d, 1H), 7.91 (s, 1H), 7.74 (d, 2H), 7.56 (d, 1H), 7.54 (s, 1H), 7.25 (m, 2H), 5.57 (m, 1H), 5.19 (d, 1H), 5.01 (d, 1H), 2.36 (s, 3H), 1.86 (m, 1H), 1.63 (m, 1H), 1.16(m, 2H). MS m/e 363.16 (MH+).

Provenance & Evidence