Hydrochloric Acid → 2-amino-4,6-dimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

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Reaction Steps

To a solution of 125 mg (0.28 mmol) of 2,4-dimethyl-6-nitro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide in 5 mL of methanol was added 220 mg (3.36 (mmol) of zinc powder followed by 3 mL of 1 N aqueous HCl. After 3 hours, the mixture was made basic with saturated aqueous sodium bicarbonate solution and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of saturated aqueous sodium bicarbonate solution and three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The oil residue was chromatographed on silica gel eluting first with dichloromethane-hexanes (1:1) and then ethyl acetate-hexanes (5-20% gradient). The material from the column was solidified from ether-hexanes with a few drops of ethanol to afford 100 mg (85%) of 2-amino-4,6-dimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide. MS: m/z 412.48 (M+1).

Provenance & Evidence