Acetyl chloride → HCID 11521901, compound

Participants

Reaction Steps

Sodium hydride (44 mg, 1.10 mmol, 60% w/w in mineral oil) was washed with hexanes and suspended in 1,4-dioxane (3 mL). A solution of 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (120 mg, 0.521 mmol), prepared in step B, above, in dioxane (2 mL) was added, and the resulting mixture was allowed to stir for 30 min. Then, acetyl chloride (45 μL, 0.63 mmol) was added by syringe, and the solution was stirred for an additional 12 h. The reaction was partitioned between water and EtOAc (20 mL each), and the organic phase was washed with brine. The aqueous phases were back-extracted in sequence with ethyl acetate, and the organic extracts were combined, dried over MgSO4, filtered and evaporated. The resulting solid was triturated with Et2O, collected by filtration and dried under vacuum to afford N-(3-cyano-1-ethyl-6-nitro-1H-indol-2-yl)-acetamide (100 mg, 71%), compound 25, as an off-white powder.

Provenance & Evidence