Chloroacetyl isocyanate → 2-[4-(2,4-dioxo-imidazolidin-1-yl)phenyl]-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

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Reaction Conditions

Reaction Steps

A solution of 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (319 mg, 1.04 mmol) in 1,4-dioxane (3 mL) was treated with chloroacetyl isocyanate (0.10 mL, 1.17 mmol), and the resulting solution was warmed to 60° C. overnight. The solution was cooled, and DBU (0.20 mL, 1.31 mmol) was added. This mixture was stirred at ambient temperature overnight, and then was partitioned between water and ethyl acetate (50 mL each). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material was triturated with ether, and the resulting solid was collected by filtration and dried under high vacuum to afford the title product (319 mg, 0.821 mmol, 79%).

Provenance & Evidence