Sodium hydride → ethyl 4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate

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Reaction Conditions

Reaction Steps

Ethyl 3-(2-fluorophenyl)-2-hydrazono-3-oxopropanoate (1.16 g, 4.87 mmol) and 1-[4-(bromomethyl)phenyl]-1H-pyrazole (1.50 g, 6.33 mmol, 1.3 equiv) were dissolved in degassed N,N-dimethylformamide (15 mL), cooled to 0° C. and treated with sodium hydride (0.312 g, 7.79 mmol, 1.6 equiv). After stirring for 1 hour at 0° C., the mixture was treated with ammonium chloride (3 mL, saturated aqueous) and water (40 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate) to provide the titled compound.

Provenance & Evidence