Aziridine → 2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(3-phenylindol-1-ylmethyl)ethyl]benzenesulfonamide

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To a solution of 48 mg (0.25 mmol) of 3-phenyl-1H-indole in 3 mL of DMF was added 28 mg (0.7 mmol) of 60% sodium hydride in mineral oil. The mixture stirred until hydrogen evolution ceased and then 73 mg (0.25 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine was added. The reaction was monitored by TLC (20% EtOAc-hexanes and 50% hexanes-CH2Cl2) indicating starting aziridine was consumed. After 30 minutes, the mixture was quenched with 7 mL of saturated aqueous ammonium chloride solution and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of saturated aqueous ammonium chloride solution and three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ether to afford 88 mg (72%) of the title compound. MS: m/z 487.59 (M+1).

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