Acetyl chloride → HCID 59425609, compound

Participants

Reaction Conditions

Reaction Steps

1-Ethyl-6-methoxy-2-(4-nitrophenyl)-1H-indole-3-carbonitrile (100 mg, 0.3 mmol), prepared by the method of example 1Gc was suspended in 1,2-dichloroethane (500 mL) at 0° C. Acetyl chloride (50 μL, 0.69 mmol) was added, followed by AlCl3 (55 mg, 0.4 mmol) in one portion. This was stirred at 0° C. for 1 hour, at room temperature for 4 hours, and at 45° C. overnight. The reaction mixture was then partitioned between CH2Cl2 and H2O. The organic layer was dried and concentrated. Purification by silica gel chromatography (195:5 CH2Cl2/EtOAc) yielded 5-acetyl-1-ethyl-6-methoxy-2-(4-nitro-phenyl)-1H-indole-3-carbonitrile (33 mg, 29%) as an orange solid.

Provenance & Evidence