1-Bromo-2-methylpropane → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]-N-(2-methylpropyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]benzenesulfonamide (137 mg, 0.299 mmol) and N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (51 mg, 0.299 mmol) in acetonitrile (2 mL) was added 1-bromo-2-methylpropane (0.065 mL, 0.598 mmol). The reaction vessel was heated at 80° C. for 8 hours. The reaction mixture was then separated between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulphate then concentrated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient) to give the title compound (100 mg) as a white foam. LCMS (2 min, formic) Rt 1.21 min, m/z (ES+) 515 (M+H).

Provenance & Evidence