Tetrahydrofuran → 4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N2-(4-methoxyphenyl)benzene-1,2-diamine

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Reaction Steps

To an aqueous solution (5.1 mL) of sodium hydrosulfite (1.15 g, 6.61 mmol) was added a mixed solution of 5-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-N-(4-methoxyphenyl)-2-nitroaniline (0.20 g, 0.41 mmol), tetrahydrofuran (4.1 mL) and ethanol (2.1 mL) at 0° C., and the resulting mixture was stirred at room temperature for 30 min. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (0.12 g, yield 71%) as a yellow oil.

Provenance & Evidence