Ethyl 4,4,4-trifluoroacetoacetate → 1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

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Reaction Conditions

Reaction Steps

A mixture of 1-methyl-3-phenyl-1H-pyrazol-5-amine (1.7 g, 9.815 mmol) and 4,4,4-Trifluoro-3-oxo-butyric acid ethyl ester (2.168 g, 11.776 mmol) in acetic acid (3.0 mL) was heated at 150° C. for 10 h in a sealed tube under constant stirring. The reaction mixture was cooled to rt and poured into rapidly stirred ice-cold water to obtain the crude product as a solid. The product was collected by filtration and dried under vacuum. The product was purified by flash-chromatography (eluent: 35% EtOAc in hexane) to yield the title compound as a white solid (0.7 g, 24%). [1H-NMR (CDCl3, 300 MHz) δ 13.65 (s, 1H), 7.52-7.37 (m, 5H), 6.78 (s, 1H), 4.20 (s, 3H); LCMS RtC=1.430 min; [M+H]+=294.0]

Provenance & Evidence