Iodine → 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

Participants

Reaction Steps

To a solution of 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.67 g, 1.99 mmol) in DMF (7 mL) was added KOH pellets (0.325 g, 5.95 mmol) followed by I2 (1 g, 3.98 mmol) in portions at 0° C. The reaction was stirred for 1 h at RT. 10% aq sodium bisulphite solution was added to the mixture and solid precipitate was obtained. The suspension was filtered and washed with H2O (2×20 mL) and dried under vacuum to give 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (800 mg, 87%) as an off brown solid. MS (ESI, pos. ion) m/z: 463.0 (M+1); 1H-NMR (300 MHz, CDCl3): δ 8.72 (brs, 1H), 8.02 (d, J=6 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.36-7.33 (m, 2H), 6.90 (d, J=8.4 Hz, 1H), 5.43 (m, 1H), 4.63 (d, J=5.7 Hz, 2H), 3.80 (s, 3H).

Provenance & Evidence