(Bromomethyl)cyclobutane → N-(cyclobutylmethyl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (150 mg, 0.374 mmol) in acetonitrile (4 mL) stirred in air at 20° C., was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (128 mg, 0.747 mmol). The reaction mixture was stirred at 20° C. for 1 hour, then (bromomethyl)cyclobutane (0.084 ml, 0.747 mmol) was added. The reaction was heated by microwaves to 150° C. for 30 minutes. After cooling the solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was washed with water (5 mL) and dried using a hydrophobic frit. The solvent was removed in vacuo to give the crude product as an orange oil. The crude product was purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title product (42 mg) as a colourless oil. LCMS (2 min, High pH) Rt 1.48 mins, m/z (ES+) 470, (M+H).

Provenance & Evidence