5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine → 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (174 mg, 0.332 mmol) in TFA (1.0 ml). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 30 min, then solvent was removed. The residue was purified with RP-HPLC to give 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (60.0 mg, 0.149 mmol, 44.7%) as an off-white solid. MS (ESI, pos. ion) m/z: 404 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.62 (1H, s), 8.90 (1H, s), 8.06-8.21 (3H, m), 7.70 (2H, d, J=4.1 Hz), 7.55-7.65 (2H, m), 7.50 (2H, d, J=8.4 Hz), 7.36 (1H, d, J=8.6 Hz), 7.16 (2H, s).

Provenance & Evidence