1-Hydroxybenzotriazole → HCID 22100913, compound

Participants

Reaction Steps

To a solution of 3-(1H-indol-5-yl)propionic acid (50 mg in 2.5 mL N,N-dimethylformamide) at 0° C. was added 43 mg 1-hydroxy-benzotriazole followed by 71 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the mixture allowed to warm to room temperature. After 23 minutes, 155 mg of 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]-ethylamine was added and the mixture stirred at room temperature for an additional hour. The reaction was then quenched by the addition of water and the mixture extracted with ethyl acetate. The combined organics were washed with water and brine, dried over sodium sulfate and the concentrated oil purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (111 mg).

Provenance & Evidence