Benzenesulfonyl chloride → HCID 9950402, compound

Participants

Reaction Steps

Sodium bis(trimethylsilyl)amide (0.23 mL, 1M inTHF, 0.23 mmol) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (Example 4e, 25.0 mg, 0.12 mmol) in THF (1.5 mL) at -78° C. and the mixture was stirred for 1 h. Phenylsulfonyl chloride (30 uL, 0.24 mmol) was added and the mixture stirred at room temperature for 2 h. prior to quenching with water (4 drops) and silica gel (~1g). Purification using solid phase extraction tubes (1000 mg silica, eluting with 0-10% 2M methanolic ammonia in dichloromethane) yielded 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1-phenylsulfonylindole (9.0 mg, 22%, HRMS-FAB+ for C20H20N2O2S: calculated MH+ : 353.13239; found: 353.13235).

Provenance & Evidence