Cesium carbonate → 4-fluoro-N-(3-methoxy-5-(prop-1-en-2-yl)pyridin-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

Potassium trifluoro(prop-1-en-2-yl)borate (53.3 mg, 0.360 mmol), N-(5-bromo-3-methoxypyridin-2-yl)-4-fluorobenzenesulfonamide (130 mg, 0.360 mmol), caesium carbonate (352 mg, 1.080 mmol), palladium(II) chloride (1.276 mg, 7.20 μmol) and triphenylphosphine (5.66 mg, 0.022 mmol) were added to a microwave vial and suspended in tetrahydrofuran (THF) (2 mL) and water (0.2 mL). The reaction vessel was sealed and heated by microwaves to 140° C. for 30 minutes. After cooling, the mixture was diluted with dichloromethane (DCM) (5 mL) and water (5 mL), then passed through a celite column. The aqueous phase was washed with further DCM (5 mL) then the organics separated using a hydrophobic frit and concentrated in vacuo to give the crude product. This was purified by flash silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient) to give the title product (75 mg). LCMS (2 min, formic) Rt 1.0 min, m/z (ES+) 323 (M+H).

Provenance & Evidence