Water → 5-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid methyl ester

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Reaction Steps

5-(5-Nitropyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester (0.750 g, 2.39 mmol) was dissolved in THF (20 mL). To the solution was added 5% Pd/C (0.10 g), and the resulting mixture was subjected to catalytic reduction for 2 hours at room temperature under atmospheric pressure. The catalyst was removed by filtration, and the filtrate was concentrated to yield of a pale yellow oil (0.677 g). This product was dissolved in THF (30 mL). To the solution were added triethylamine (0.333 mL, 2.39 mmol), subsequently 3,4-Dichlorobenzoyl chloride (0.501 g, 2.39 mmol) and the resulting solution was stirred for 1 hour at room temperature. Water (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (30 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate to yield 1.00 g of the title compound as a white powder.

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