Benzoyl chloride → HCID 15462189, compound

Participants

Reaction Steps

Benzoyl chloride (0.10 mL, 0.86 mmol) was added to a solution of (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (Example 3g, ~75 mg, 0.24 mmol), triethylamine (0.20 mL, 1.4 mmol) and DMAP (23 mg, 0.19 mmol) in dichloromethane (2.5 mL). The mixture was stirred for 15 h. prior to quenching with water (25 mL) and extraction into dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Purification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform (1.5-3.3%) yielded (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-benzoylindole (20.1 mg, 20%, HRMS-FAB+ for C27H32N2O2 : calculated MH+ :417.25421; found MH+ :417.25475).

Provenance & Evidence