Phenyl Methylcarbamate → HCID 86730364, compound

Participants

Reaction Steps

4-((6-(3-Fluoropropoxy)-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 33-5 (49.4 mg, 0.164 mmol) was dissolved in N,N-dimethylformamide (1.6 mL), 50-72% oily sodium hydride (14.9 mg) was added under nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled to 0° C. again, phenyl methylcarbamate described in Production Example 1-7 (62.0 mg, 0.41 mmol) was added, and the mixture was stirred at room temperature for 3.5 hours. A saturated aqueous ammonium chloride solution, water, and ethyl acetate were added to the reaction mixture for partition. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was concentrated under vacuum, and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:4-0:1-ethyl acetate:methanol=99:1-9:1). The target fraction was concentrated under vacuum to obtain the title compound (34.4 mg, 59%).

Provenance & Evidence