Potassium Phosphate, Tribasic → 5-(3-(6-fluoropyridin-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 (500 mg, 0.811 mmol) and 6-fluoropyridine-2-boronic acid pinacol ester (226 mg, 1.014 mmol) in p-dioxane/H2O (4:1, 7.5 mL) followed by potassium phosphate (430 mg, 2.028 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (28.7 mg, 0.041 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 5-15% EtOAc in DCM with 1% MeOH) to give 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (418 mg, 0.714 mmol, 88%) as a yellow solid. MS (ESI, pos. ion) m/z: 378 (M+1).

Provenance & Evidence