Methyl iodide → tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)-phenyl)benzo[d]isoxazol-3-yl)(methyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)phenyl)benzo[d]isoxazol-3-yl)carbamate (1.09 g, 1.39 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (0.061 g of a 60% dispersion in mineral oil, 1.53 mmol) and the reaction mixture was stirred for 10 minutes at ambient temperature. Iodomethane (87 μL, 1.39 mmol) was added and the reaction mixture for stirred for 30 minutes at ambient temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and saturated aqueous ammonium chloride (10 mL). The organic phase was washed with water (2 5 mL) and brine (10 mL) dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with a 0-50% gradient of ethyl acetate in hexanes to afford tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)-phenyl)benzo[d]isoxazol-3-yl)(methyl)carbamate as a colorless foam.

Provenance & Evidence