Sodium hydride → HCID 69671081, compound

Participants

Reaction Steps

To a solution of 5-methoxy-2-phenylindole (205 mg) in N,N-dimethylformamide (4.6 mL) was added sodium hydride (in oil, 50 to 72%, 55 mg) under cooling with ice and an argon atmosphere, and the mixture was stirred at room temperature for 2 hours. Then methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (193 mg) was added, and the mixture was stirred at 80° C. for 22 hours. The reaction mixture was allowed to cool to ambient temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (229 mg).

Provenance & Evidence