Triethylamine → 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

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Methanesulfonyl chloride (0.042 mL, 0.54 mmol) was added to a solution of 5-(1-hydroxycyclohex-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13a, 50.6 mg, 0.16 mmol) and triethylamine (0.15 mL, 1.06 mmol) in dichloromethane (2.5 mL) at 0° C. The reaction was allowed to warm slowly to room temperature and stirring was continued overnight. The reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with water and brine, dried over sodium sulfate and the solvent was removed in vacuo. Flash chromatography (silica, 5-8% 2M methanolic ammonia in dichloromethane) yielded 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (21.8 mg, 46%); HRMS-FAB+ for C20H26N2 :calculated MH+ :295.21744; found MH+ :295.21953.

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