Iodine → HCID 68328821, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 0.6148 mmol) in DMF (1.5 mL) was added 1.2M aq. KOH (1.5 mL) and the reaction was stirred at 0° C. for 5 min. I2 (234 mg, 0.9297 mmol) was added and the mixture was stirred for additional 1 h. The reaction was quenched with H2O (10 mL) to get a pink precipitate. The precipitate was filtered, washed with H2O (6 mL) and dried. The crude product was purified with silica-gel column chromatography (eluent: 50% EtOAc in petroleum ether) to give 5-(3-iodo-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (140 mg, 61%) as a pink solid. MS (ESI, pos. ion) m/z: 369.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.85 (brs, 1H), 7.68 (m, 2H), 7.65 (m, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 3.70-3.75 (m, 1H), 1.20 (d, J=6.4 Hz, 6H).

Provenance & Evidence