Sodium Iodide → Ethyl 3-{[(4-{[cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate

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Reaction Conditions

Reaction Steps

To a mixture of 3-[chloro(cyclohexyl)methyl]-6-methoxy-2-methyl-1-benzofuran (530 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate (498 mg) synthesized in Example 2(2) and N,N-dimethylformamide (10 mL) were added sodium iodide (408 mg) and sodium carbonate (288 mg), and the mixture was stirred at 80° C. overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (781 mg, 85%) as a white solid.

Provenance & Evidence