Water → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamide

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Reaction Steps

5-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.31 g, 1.44 mmol) was dissolved in pyridine (3 mL), ethane sulfonyl chloride (0.12 mL, 1.3 mmol) was added, the mixture was stirred for 4 hours, and then water was added. The mixture diluted with ethyl acetate and the mixture was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. Flash chromatography (5%-50% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamide (0.127 g). HPLC purity 100% at 210-370 nm, 8.3 min.; the Xterra™ RP18 instrument, 3.5/, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min., hold 4 min. HRMS: calcd for C14H14FN3O2S+H+, 308.08635; found (ESI, [M+H]+), 308.0855.

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