5-Fluoroindole-2-carboxylic acid → HCID 9035231, compound

Participants

Reaction Steps

Treat 5-fluoro-1H-indole-2-carboxylic acid 3 (X═F, 1.7 g, 9.5 mmol) with piperidine as described in General Synthetic Procedure VIa to afford 5-fluoro-1H-indol-2yl-piperidin-1-yl-methanone 8 (X═F, R4=piperidin-1-yl; 2.3 g, 100%) as a white solid. 1H NMR (DMSO-d6) δ 11.7 (brs, 1H), 7.5-7.3 (m, 2H), 7.1-7.0 (m, 1H), 6.7 (s, 1H), 3.7 (m, 4H), 1.7-1.5 (m, 6H). Treat 5-fluoro-1H-indol-2yl-piperidin-1-yl-methanone (125 mg, 0.51 mmol) with 2-aminophenyldisulfide (347 mg, 1.4 equiv.) as described in General Synthetic Procedure VIIa to afford the title compound Iac (92 mg, 25%) as an ivory-colored solid, m/z=369 (M+1).

Provenance & Evidence