Potassium Carbonate → HCID 69481076, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-(3-chloropropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (24 mg, 0.057 mmol) in N,N-dimethylformamide (700 μL) was added succinimide (23 mg, 0.23 mmol), potassium carbonate (32 mg, 0.23 mmol), and possium iodide (38 mg, 0.23 mmol), respectively. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was cooled and quenched with cold 1 N aqueous hydrochloric acid and extracted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 1-[3-(2,5-dioxo-1-pyrrolidinyl)propyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1 H), 7.31 (s, 1 H), 7.19 (dd, J=8.5, 5.3 Hz, 2 H), 7.04 (t, J=8.6 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.17-4.12 (m, 4 H), 3.58 (t, J=7.1 Hz, 2 H), 2.71 (s, 4 H), 1.90 (m, 2 H), 1.47 (t, J=7.1 Hz, 3 H); MS m/z 504 (M+Na)+.

Provenance & Evidence