Hydrochloric Acid → HCID 67072424, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5,8-difluoro-1-(4-iodobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.200 g, 0.426 mmol) and benzimidazole (0.252 g, 2.13 mmol) in 3 mL of dimethylsulfoxide under nitrogen was added 8-hydroxyquinoline (0.013 g, 0.085 mmol), 1 N cesium carbonate (0.852 mL, 0.852 mmol), and copper(I)iodide (0.041 g, 0.21 mmol). The reaction vessel was covered with aluminum foil and heated to 95° C. for 24 hours. The reaction mixture was cooled to room temperature, and saturated aqueous lithium hydroxide (20 drops) was added. After 10 hours, 6 N HCl was added to pH ˜4. The reaction mixture was filtered and purified via reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 432.1 for M+H+. 1H NMR (400 MHz, d6-DMSO) δ 9.21 (s, 1H), 7.84-7.70 (m, 2H), 7.67 (d, J=8.2 Hz, 2H), 7.62 (bs, 1H), 7.43 (m, 3H), 7.32-7.26 (m, 3H), 5.99 (d, J=3.5 Hz, 2H).

Provenance & Evidence