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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A suspension of Raney nickel (1 g) and the product from Step E above (18.2 g, 52.9 mmol) in ethanol (130 mL) was placed on a Parr shaker apparatus and hydrogenated at 40 psi hydrogen overnight. The suspension was filtered through Celite and the filtrate was evaporated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 8.83 (s, 1H), 7.89 (s, 1H), 7.82 (s, 1H), 4.83 (d, J=16 Hz, 1H), 4.72 (s, 1H), 4.49 (d, J=16 Hz, 1H), 1.45 (s, 9H).

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