Potassium Phosphate, Tribasic → HCID 71259332, compound

Participants

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 (0.500 g, 0.876 mmol), potassium phosphate (0.651 g, 3.07 mmol), and bis(tri-t-butylphosphine)palladium(0) (0.045 g, 0.088 mmol). The vial was flushed with Ar, then 1,4-dioxane (6.57 ml) and water (2.191 ml) were added in sequence, followed by 2-chloro-1-iodo-4-(trifluoromethyl)benzene (0.426 ml, 2.63 mmol). The vial was sealed and stirred at room temperature 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 (RediSep Gold (Teledyne Isco, Lincoln, Nebr.) 40 g, gradient elution 0-100% EtOAc/Heptane) to afford 3-(2-chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.405 g, 0.650 mmol, 74.2% yield) as a light yellow solid. m/z (ESI) 624.0 (M+H)+.

Provenance & Evidence