Sodium Carbonate → N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-phenylthiophene-2-sulfonamide

Participants

Reaction Steps

Sodium carbonate (2 mL of a 2 M aqueous solution) followed by phenyl boronic acid (86 mg, 0.71 mmol) in 2 mL of 95% ethanol were added to a solution of N-(methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (200 mg, 0.47 mmol) and tetrakis(triphenylphosphine)palladium (0) (23 mg, 0.02 mmol) in dry benzene (4 mL) under argon. The mixture was refluxed for 12 h, diluted with 5 mL of water and extracted into ethyl acetate (3×25 mL). The combined organic extracts was washed with brine (1×25 mL), dried and evaporated. The residue was flash chromatographed on silica gel using 25% ethyl acetate/hexanes to afford 123 mg (62%) of the sulfonamide as a colorless gum.

Provenance & Evidence