Sodium ethoxide → Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

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Reaction Steps

Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate (477 mg, 0.99 mmol) was dissolved in ethanol (50 mL) and sodium ethoxide (0.91 mL of a 2.4 M solution) was added. The solution was stirred until reaction was determined complete by LC-MS and the suspension was concentrated under reduced pressure. A small amount of water was added and the mixture was acidified with 1 N hydrochloric acid to a pH of 3 and the resulting white solid was collected by vacuum filtration to yield ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (368 mg, 85% yield). 1H NMR (methanol-d4/CDCl3) δ 8.19 (s, 1 H), 7.17-7.06 (m, 4 H), 6.94-6.83 (m, 4 H), 6.58 (s, 1 H), 4.26 (q, J=7.2 Hz, 2 H), 3.81 (s, 2 H), 1.27 (t, J=7.2 Hz, 3 H); MS m/z 459 (M+23).

Provenance & Evidence