Benzenesulfonyl chloride → HCID 15462187, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (0.19 mL, 1.45M in hexane, 0.28 mmol) was added to a solution of (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (Example 3g, 77.1 mg, 0.25 mmol) in THF (1 mL) at -78° C.; the temperature was raised to 0 ° C. and the mixture was stirred for 40 min. After recooling to -78° C., phenylsulfonyl chloride (60 μL, 0.47 mmol) was added and the mixture was allowed to warm to room temperature slowly (overnight). The mixture was quenched with water (5 mL) and extracted into dichloromethane. The organic layer was washed sequentially with water and brine, and dried over sodium sulfate. Purification by flash chromatography (silica gel, 1-4% 2M methanolic ammonia in chloroform) yielded (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (19.1 mg, 17%, HRMS-FAB+ for C26H32N2O3S: calculated MH+ :453.22119; found MH+ :453.22550).

Provenance & Evidence