Hydrochloric Acid → HCID 44816722, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-fluoro-1-(4-iodobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.060 g, 0.13 mmol), pyrrolidine-2-one (0.034 g, 0.40 mmol), 8-hydroxyquinoline (1.9 mg, 0.013 mmol) and potassium carbonate (0.037 g, 0.27 mmol) in 2 mL of DMF under nitrogen was added copper(I)iodide (10 mol %). The reaction mixture was heated to 100° C. for 22 hours, then cooled to room temperature. To the mixture was added 1 N NaOH (0.30 mL, 0.30 mmol). After 2 hours, the mixture was acidified with 6 N HCl to pH ˜2, diluted with DMSO (2 mL), filtered, and purified via reverse phase HPLC to provide the title compound which gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 381.1 for M+H+: 1H NMR (400 MHz, d6-DMSO) δ 9.25 (s, 1H), 7.86-7.80 (m, 1H), 7.66-7.64 (m, 3H), 7.36 (dd, J=8.1 Hz, 3.4 Hz, 1H), 7.30 (d, J=8.7 Hz, 2H), 5.81 (s, 2H), 3.78 (t, J=7.1 Hz, 2H), 2.51-2.44 (m, 2H), 2.07-2.01 (m, 2H).

Provenance & Evidence