Potassium Phosphate, Tribasic → 5-(3-(2,4-difluorophenyl)-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine

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Reaction Conditions

Reaction Steps

A mixture of potassium phosphate (0.089 g, 0.42 mmol), 2,4-difluorophenylboronic acid pinacol ester (0.040 g, 0.17 mmol, Aldrich), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (5 mg, 7 μmol), 5-(3-iodo-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (0.05 g, 0.14 mmol), and IPA/H2O (70%, 0.5 mL) was heated in a microwave at 120° C. for 10 min. The aqueous layer was removed and the organic layer was purified by preparative HPLC (10-90% MeCN/water/0.1% NH4OH) to give 5-(3-(2,4-difluorophenyl)-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine as a tan solid. MS (ESI, pos. ion) m/z: 343 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 8.06 (1H, s), 7.64-7.73 (2H, m), 7.56-7.61 (2H, m), 7.06-7.14 (2H, m), 3.14 (3H, s).

Provenance & Evidence