Water → 4-((6-(2-Methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine

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Reaction Conditions

Reaction Steps

N-(4-((6-(2-methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 20-5 (3.45 g, 10.1 mmol) was dissolved in methanol (50 mL), a 2 M sodium hydroxide solution (50 mL) was added at room temperature, and the mixture was heated and stirred at 70° C. for 3 hours. Water and ethyl acetate were added to the reaction mixture for partition. The aqueous layer was extracted with ethyl acetate three times and the combined organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under vacuum and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=49:1-24:1). The target fraction and the mixture fraction were concentrated under vacuum separately from each other, the mixture fraction was purified again with silica gel column chromatography (ethyl acetate:methanol=1:0-9:1), and then the resultant was combined with the above-described target fraction to obtain the title compound (2.60 g, 86%).

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