Potassium Phosphate, Tribasic → 5-(3-(6-chloropyridin-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-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (300 mg, 0.487 mmol) and 6-chloropyridine-2-boronic acid pinacol ester (175 mg, 0.730 mmol) in p-dioxane/H2O (4:1, 5 mL) followed by bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (17.23 mg, 0.024 mmol) and potassium phosphate (310 mg, 1.460 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. 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-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (265 mg, 0.440 mmol, 90%) as a yellow solid. MS (ESI, pos. ion) m/z: 602 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (1H, d, J=1.4 Hz), 8.14 (1H, s), 8.05 (1H, d, J=8.8 Hz), 7.92 (1H, dd, J=8.7, 1.7 Hz), 7.81 (2H, d, J=8.2 Hz), 7.68-7.75 (1H, m), 7.59-7.66 (1H, m), 7.33 (2H, d, J=8.6 Hz), 7.24 (2H, d, J=3.7 Hz), 6.90 (2H, d, J=8.8 Hz), 4.54 (2H, s), 3.81 (3H, s), 2.35 (3H, s).

Provenance & Evidence