5,6,7-Trimethoxy-1H-indole-2-carboxylic acid → HCID 19050056, compound

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Reaction Steps

To 42.6 mg(95 μmol) of methyl 3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate, 1.6 ml of 3M hydrogen chloride-ethyl acetate was added, and the mixture was stirred at room temperature for one hour. Then the solvent was distilled off. The residue with 23.8 mg (95 mol) of 5,6,7-trimethoxyindole-2-carboxylic acid, and 54.6 mg (285 μmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was stirred in 0.95 ml of anhydrous dimethylformamide at room temperature under atmosphere of argon overnight. Water was added to the liquid reaction mixture. The resulting mixture was extracted with methylene chloride, and the extract solution was washed with water, 10% sodium hydrogencarbonate, and saturated sodium chloride solution successively, and dried over anhydrous sodium sulfate. Therefrom the solvent was distilled off. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain methyl 1-chloromethyl-5-hydroxy-7-trifluoromethyl-3-(5,6,7-trimethoxy-1H-indol-2-ylcarbonyl)-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 45.3 mg (82%).

Provenance & Evidence