Ammonium Chloride → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide

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Reaction Steps

To a stirred mixture of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanoic acid (230 mg; 0.68 mmol), ammonium chloride (180 mg, 3.4 mmol), 1-hydroxy-7-azabenzotriazole (92 mg, 0.68 mmol), anhydrous acetonitrile (5 mL), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (325 mg, 1.7 mml) was added diisopropylethylamine (0.47 mL, 2.7 mmol). The mixture was stirred under nitrogen at rt for 22 hr before concentrated in vacuo. The residue was mixed with saturated aqueous sodium bicarbonate solution (15 mL) and extracted with dichloromethane (2×10 mL). The combined dichloromethane extracts were dried (Na2SO4). Flash chromatography (SiO2 Column, 10-100% ethyl acetate in hexanes) gave 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide (169 mg, 0.50 mmol, 74% yield) as a white solid.

Provenance & Evidence