N-Iodosuccinimide → tert-butyl 3-(3-iodo-1H-indol-5-yl)-1,2,4-thiadiazol-5-ylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl (3-(1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (100 mg, 0.316 mmol) in THF (5 mL) at 0° C. was added N-iodosuccinimide (78 mg; 0.348 mmol) and the reaction was stirred for 1 h at RT. The mixture was treated with saturated aq. NaHSO3 solution (5 mL). The volatile solvent were evaporated and the crude residue was further treated with ice-cold water and petroleum ether to give tert-butyl (3-(3-iodo-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (80 mg, 58.8%) as an off white solid. MS (ESI, pos. ion) m/z: 386.9 (M+1) (carbamic acid mass); 1H NMR (400 MHz, DMSO-d6): δ 12.42 (brs, 1H), 11.76 (brs, 1H), 8.15 (s, 1H), 8.00-7.98 (m, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.49 (d, J=8.8 Hz, 1H), 1.51 (s, 9H).

Provenance & Evidence