Potassium Phosphate, Tribasic → HCID 90388211, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.200 g, 0.351 mmol), potassium phosphate (0.260 g, 1.227 mmol), and PdCl2(dppf)-CH2Cl2 (0.029 g, 0.035 mmol). DMF (0.150 mL) was added, followed by 1,3-dibromo-5-(trifluoromethyl)benzene (0.166 ml, 1.052 mmol). The vial was flushed with argon, sealed, and stirred at 85° C. for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (silica gel, gradient elution 0 to 75% EtOAc:Hexane) to afford 3-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.081 g, 0.121 mmol, 34.6% yield) as a white solid. m/z (ESI) 668.0 (M+H)+.

Provenance & Evidence