Imidazole → HCID 58169435, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-N-(2-hydroxyethyl)thiophene-2-sulfonamide (1.3 g, 4.54 mmol) in dry CH2Cl2 (40 mL) was added imidazole (0.371 g, 5.45 mmol, 1.2 eq). The reaction mixture was stirred at 0° C. for 5 min and tert-butylchlorodimethylsilane (0.82 g, 5.45 mmol, 1.2 eq) was added in one portion. The solution was stirred at 0° C. for another 1 h and allowed to warm to room temperature within 2 h. The reaction mixture was evaporated under reduced pressure and the resulting residue was dissolved in EtOAc. The EtOAc solution was washed with 1 N HCl, saturated NaHCO3, and brine, dried (Na2SO4) and filtered. The filtrate was concentrated by evaporation to afford 5-bromo-N-(2-(tert-butyldimethyl silyloxy)ethyl) thiophene-2-sulfonamide (600 mg, 55%). LC-MS (m/z)=400.0 [M+H]+.

Provenance & Evidence