1-Bromo-2-methylpropane → N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-vinylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-chloro-2-fluorophenyl)-4-vinylbenzenesulfonamide (822 mg, 2.64 mmol) in acetonitrile (10 mL) stirred in air at 20° C., was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (903 mg, 5.27 mmol). The reaction mixture was stirred at 20° C. for 2 hours. 1-bromo-2-methylpropane (0.573 mL, 5.27 mmol) was then added and the reaction vessel sealed and heated by microwaves (Emrys Optimiser) to 150° C. for 30 minutes. After cooling, the reaction mixture was concentrated in vacuo and redissolved in ethyl acetate. The organic phase was washed with water (10 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a yellow oil which solidified. The crude was purified by silica (Si) chromatography using a 0-50% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 824 mg as a colourless oil. LCMS [LCMS2] Rt 1.46 min, m/z (ES+) 368 (M+H).

Provenance & Evidence