Isopropylamine → HCID 68327956, compound

Participants

Reaction Steps

To a solution of 5-(1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (200 mg, 0.995 mmol) in DMF (2 mL) was added isopropyl amine (0.169 mL, 1.99 mmol), diphenyl ether (161 mg, 0.995 mmol), and DIPEA (0.34 mL, 1.99 mmol) and the reaction was stirred at RT for 5 min. To the above mixture at RT was added BOP reagent (461 mg, 1.045 mmol) and the reaction was further stirred for 18 h at RT. The mixture was treated with H2O (10 mL) to get off white precipitate. The precipitate was filtered, washed with H2O (10 mL) and dried. The solid was further triturated with petroleum ether (2×5 mL) to afford 5-(1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 62%) as an off white solid. MS (ESI, pos. ion) m/z: 243.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.40 (brs, 1H), 7.98 (s, 1H), 7.59 (dd, J=6.8, 1.6 Hz, 1H), 7.51 (t, J=7.2 Hz, 2H), 7.44 (m, 1H), 3.70-3.75 (m, 1H), 1.22 (d, J=6.4 Hz, 6H).

Provenance & Evidence