Pyridine → N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-2,6-dimethylbiphenyl-4-sulfonamide

Participants

Reaction Steps

2,6-Dimethylbiphenyl-4-sulfonyl chloride (0.147 g, 0.53 mmol, 1.4 equiv.) and pyridine (0.152 ml, 1.87 mmol, 5.0 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1.5 ml) and the mixture stirred at room temperature for 3 hours. 5-Bromo-thiazol-2-ylamine hydrobromide (97 mg, 0.38 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The product was extracted into dichloromethane (2 ml), dried over sodium sulfate and evaporated to a brown gum. The gum was purified by preparative HPLC to give N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-2,6-dimethylbiphenyl-4-sulfonamide, 15 mg (9% yield). LC @UV215 nm; Rt 2.64: 96%, m/z (ES+): 467, 468 (M+H).

Provenance & Evidence