1-Hydroxybenzotriazole → 7-Nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

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Reaction Steps

A solution of 7-nitro-1H-indole-2-carboxylic acid (4.4 g), 1H-1,2,3-benzotriazol-1-ol (3.8 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (4.8 g), 2-(tritylthio)ethylamine hydrochloride (7.4 g) and triethylamine (3.5 mL) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was crystallized from diethyl ether-hexane to give the title compound (10.1 g, yield 95%) as yellow crystals.

Provenance & Evidence