Phenyl Methylcarbamate → HCID 86730313, compound

Participants

Reaction Steps

4-((6-Methoxy-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 1-4 (1.7 g, 6.66 mmol) was dissolved in N,N-dimethylformamide (25 mL), 50-72% oily sodium hydride (424 mg) was added under nitrogen atmosphere at 0° C., and then the mixture was stirred at room temperature for 45 minutes. The mixture was cooled to 0° C. again, phenyl methylcarbamate described in Production Example 1-7 (1.64 g, 10.8 mmol) was added, and the resultant was stirred at room temperature for 3 hours. A saturated aqueous ammonium chloride solution, water, and ethyl acetate were added to the reaction mixture for partition. The aqueous layer was extracted with ethyl acetate once and the combined organic layer was washed with water and a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered off, then the filtrate was concentrated under vacuum, and then the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:3-0:1-ethyl acetate:methanol=99:1-19:1). The target fraction was concentrated under vacuum and then the precipitate was collected by filteration and washed with ethyl acetate to obtain the title compound (1.37 g, 66%). The mixture fraction was concentrated under vacuum and purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol—99:1-19:1). The target fraction was concentrated under vacuum, and then the precipitate was collected by filteration and washed with ethyl acetate twice to obtain the title compound (387 mg, 19%).

Provenance & Evidence