4-Fluorobenzenesulfonyl chloride → 4-fluoro-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

Participants

Reaction Steps

5-isopropyl-3-methylpyridin-2-amine (142 mg, 0.945 mmol) and 4-fluorobenzene-1-sulfonyl chloride (221 mg, 1.13 mmol) were dissolved in pyridine (3 mL) and left to stand overnight. Another 1 eq of 4-fluorobenzene-1-sulfonyl chloride was added to the mixture and the reaction left to stand for a further 6 hours. The reaction was concentrated in vacuo and the crude product extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid. The organic phase was then passed through a hydrophobic frit, concentrated in vacuo and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The relevant fractions were then combined and evaporated to give the title compound (127 mg). LCMS (2 min, formic) Rt 1.03 min, m/z (ES+) 309 (M+H).

Provenance & Evidence