Cyanomethylenetributylphosphorane → 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(oxetan-3-ylmethyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (100 mg, 0.340 mmol) and oxetan-3-ylmethanol (20.95 mg, 0.238 mmol) in toluene (1.5 mL) stirred in air at room temperature was added a solution of 2-(tributylphosphoranylidene)acetonitrile (82 mg, 0.340 mmol) in toluene (0.5 mL). The reaction mixture was stirred at 20° C. for 16 hours. Additional 2-(tributylphosphoranylidene)acetonitrile (82 mg, 0.340 mmol) and oxetan-3-ylmethanol (20.95 mg, 0.238 mmol) were added and the solution stirred for a further 24 hours. The reaction solution was then purified on an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with a 0-50% ethyl acetate-cyclohexane gradient, to give the title product (63 mg) as a colourless gum. LCMS (2 min, formic) Rt 1.12 min, m/z (ES+) 365 (M+H).

Provenance & Evidence