Dichloromethane → 5-(2-Bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-YL)naphthalene-2-sulfonamide

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Reaction Steps

To a solution of 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (3.27 g, 4.92 mmol) in DCM (49.2 mL, 4.92 mmol) was added TFA (1.896 mL, 24.60 mmol). The resulting mixture was stirred at room temperature. After 30 min, LC/MS showed mainly desired product. The mixture was stirred for an additional hour at room temperature until the reaction was complete. The mixture was partially concentrated until a white solid crashed out. The solid was filtered, washed with diethyl ether and dried to afford 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (2.4 g, 4.67 mmol). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.58 (d, J=8.76 Hz, 1H) 7.68-7.74 (m, 1H) 7.74-7.83 (m, 2H) 7.87 (d, J=8.01 Hz, 1H) 8.16-8.24 (m, 2H) 8.34 (d, J=8.34 Hz, 1H) 8.52-8.57 (m, 2H); m/z (ESI) 513.7 (M+H)+.

Provenance & Evidence