Hydrochloric Acid → methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate

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Reaction Steps

A solution of methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate (0.020 g, 0.037 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, then the residue was added with an excessive amount of triethylamine, and the mixture was azeotroped with toluene. The resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate (0.007 g, 43%).

Provenance & Evidence