Ammonium Chloride → HCID 52914043, compound

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium bromide (3.00 M in diethyl ether, 0.135 mL, 0.404 mmol, 2.00 equiv) was added to a solution of N-(1-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}-1-methylethyl)-2,2,2-trifluoroethanesulfonamide (100 mg, 0.202 mmol, 1 equiv) in tetrahydrofuran (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 5 minutes, then was treated with saturated aqueous ammonium chloride solution. The biphasic mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (hexanes, grading to 90% ethyl acetate-hexanes) to afford N-[1-(3-{1-ethyl-5-[4-(1-hydroxyethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (79 mg, 77%). Calcd (M+1)+: 512.2. Found: 512.1.

Provenance & Evidence