Tetrahydrofuran → HCID 4777838, compound

Participants

Reaction Steps

To a solution of 1H-indole-2-carboxylic acid 3 (X═H, 1.0 g, 6.21 mmol) and anhydrous THF (50 ml), add carbonyldiimidazole (1.10 equiv., 1.1 g, 6.83 mmol). Stir for 30 min at rt and then add MeNH2HCl (1.30 equiv., 541 mg, 8.07 mmol) in one portion. Add DMF (10 mL) to the reaction and stir at rt. After 2 h, pour the clear yellow reaction solution into H2O. Collect the precipitate by filtration and dry under vacuum at 40° C. to afford 1H-indole-2-carboxylic acid methylamide 4 (X═R2═H, R3═CH3; 860 mg, 80%) as a yellow solid, mp 222-223° C.; 1H NMR (DMSO-d6) δ 11.6 (brs, 1H), 8.45 (m, 1H), 7.60 (d, 1H, J=7.8 Hz), 7.44 (dd, 1H, J=1.05, 8.25 Hz), 7.20-7.14 (m, 1H), 7.60-7.00 (m, 1H), 2.82 (d, 3H, J=4.2 Hz). m/z obs=175 (M+1). Treat 1H-indole-2-carboxylic acid methylamide (174 mg, 1.0 mmol) with phenyldisulfide (1.1 equiv., 240 mg, 1.1 mmol) as described in General Synthetic Procedure VIIa to afford the title compound Ij (140 mg, 50%) as an ivory-colored solid, mp 201-204° C.; 1H NMR (DMSO-d6) δ 12.3 (brs, 1H), 8.3 (m, 1H), 7.48 (d, 1H), 7.42 (d, 1H), 7.3-7.0 (m, 7H), 2.9 (d, 3H).

Provenance & Evidence