1-Bromo-2-methylpropane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(5-methylpyridin-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-cyano-2-pyridinyl)-4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonamide (23 mg, 0.060 mmol) in acetonitrile (0.5 mL) at room temperature was added N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (0.024 mL, 0.120 mmol). The reaction mixture was stirred at 20° C. for 1 hour, then 1-bromo-2-methylpropane (0.013 mL, 0.120 mmol) was added. The reaction was heated by microwaves to 150° C. for 30 minutes. After cooling, the reaction mixture was diluted with methanol and passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge followed by a sulphonic acid (SCX) SPE cartridge, eluting with methanol. The appropriate fractions were combined and evaporated under a stream of nitrogen to give the crude product. The crude was purified by mass directed autoprep (formic acid modifier), to provide the title compound (1.8 mg). LCMS (2 min, formic) Rt 1.25 min, m/z (ES+) 441 (M+H).

Provenance & Evidence