tert-Butyl Methyl [3-Cyano-5-(trifluoromethyl)pyridin-2-yl]malonate → Tert-butyl 7-oxo-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-8-carboxylate

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To a solution of tert-butyl methyl [3-cyano-5-(trifluoromethyl)pyridin-2-yl]malonate (4.02 g, 11.7 mmol) in ethanol (60 mL) was added a slurry of Raney Nickel (0.60 g, 10 mmol). The mixture was placed on a Parr apparatus and hydrogenated under hydrogen at 40 psi overnight. The suspension was filtered through celite and the filtrate was evaporated in vaccuo to afford 3.68 g (99.6%) of the desired product as a yellow oil. LC-MS calculated for C14H15F3N2O3: (M+H)+317; found 217.1 (M−CO2tBu+H+1)+.

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