Acetyl chloride → N-(2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine (Intermediate 24, 9.6 g, 30 mmol) in DCM (100 mL) was treated with triethylamine (12.8 mL, 91.0 mmol) and 4-dimethylaminopyridine (1.9 g, 15 mmol). The solution was cooled to 0° C. and acetyl chloride (4.3 mL, 61 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and washed with saturated aqueous NaHCO3 (50 mL) and 1 M HCl (2×50 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (10.3 g). MS m/z 359 [M+H]+.

Provenance & Evidence