Triethylamine → 1H-Indole-3-carbonyl azide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1H-indole-3-carboxylic acid (500 mg) in tetrahydrofuran (10 mL) were added triethylamine (0.519 mL) and diphenylphosphoryl azide (0.802 mL) at ambient temperature. The mixture was stirred at 60° C. for 2 hours. Ethyl acetate (10 mL) was added to the mixture at room temperature, and then the organic layer was washed with saturated sodium bicarbonate aqueous solution×2, water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residual solid was recrystallized from ethyl acetate (2 mL). The crystals were washed with n-hexane/chloroform (3:1, 1 mL). The crystals were recrystallized from ethyl acetate again to afford 1H-indole-3-carbonyl azide (192 mg) as white crystals.

Provenance & Evidence