4-Fluorobenzenesulfonyl chloride → N-(5-bromo-3-methoxypyridin-2-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-3-methoxypyridin-2-amine (100 mg, 0.493 mmol) in pyridine (1 mL) stirred in air at room temperature was added a solution of 4-fluorobenzene-1-sulfonyl chloride (115 mg, 0.591 mmol) in pyridine (1 mL). The reaction mixture was stirred at 20° C. for 16 hours then the solvent was evaporated in vacuo to give the crude product. The crude was passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol followed by 2M ammonia/methanol, then a sulphonic acid (SCX) SPE cartridge eluting with methanol followed by 2M ammonia/methanol. The appropriate fractions were combined and evaporated under a stream of nitrogen to give the crude product. Final purification by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-20% methanol gradient), gave the title product (133 mg) as an off-white solid. LCMS (2 min, formic) Rt 1.03 min, m/z (ES+) 361/363 (M+H).

Provenance & Evidence