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

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (245 mg, 0.407 mmol) and 4-chlorophenylboronic acid (95 mg, 0.610 mmol) in p-dioxane/H2O (4:1, 4.5 mL) followed by potassium carbonate (168 mg, 1.221 mmol) and Pd(PPh3)4 (23.5 mg, 0.020 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 105° C. for 30 min. The mixture was diluted with DCM and washed with H2O and separated. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0-20% EtOAc in DCM) to give 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (230 mg, 0.339 mmol, 83%) as a light yellow solid. MS (ESI, pos. ion) m/z: 678 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.98 (1H, d, J=1.4 Hz), 8.15 (1H, s), 8.05-8.13 (3H, m), 7.98-8.03 (1H, m), 7.80-7.88 (3H, m), 7.66 (2H, d, J=8.2 Hz), 7.48 (2H, d, J=8.6 Hz), 7.33 (2H, d, J=8.6 Hz), 7.24 (2H, s), 6.89 (2H, d, J=8.6 Hz), 4.55 (2H, s), 3.80 (3H, s), 2.35 (3H, s).

Provenance & Evidence