Citric Acid → methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-3-yl)methyl]benzyl}amino)phenyl]propanoate

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Reaction Steps

Under ice-cooling, sodium hydride (60% in oil, 0.436 g, 10.9 mmol) was added to a solution of 2-phenylindole (2.11 g, 10.9 mmol) in N,N-dimethylformamide (5 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 1 hr. To the reaction mixture was added dropwise a solution of methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (3.65 g, 7.26 mmol) in N,N-dimethylformamide (5 mL), and the mixture was allowed to warm to room temperature and stirred for 3 hr. Water and 10% aqueous citric acid solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give a mixture (1.53 g, yield 32%) of the title compound and methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate as a brown oil.

Provenance & Evidence