8-Hydroxyquinoline → HCID 24983815, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzyl-5-bromothiophene-3-carboxamide (0.57 g, 1.91 mmol), 4-(benzyloxy)pyridin-2(1H)-one (0.42 g, 2.10 mmol), copper(I) iodide (0.055 g, 0.29 mmol), 8-hydroxyquinoline (0.042 g, 0.29 mmol) and potassium carbonate (0.40 g, 2.87 mmol) in N,N-dimethylformamide (15 mL) was stirred at 130° C. for 17 h under nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, and then diluted with ethyl acetate (50 mL). The organic layer was washed with water (2×25 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 10-80% ethyl acetate in hexanes to afford the title compound as a white solid (0.14 g, 18%): mp 162-163° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (t, J=6.0 Hz, 1H), 8.07 (d, J=7.9 Hz, 1H), 8.00 (d, J=1.5 Hz, 1H), 7.71 (d, J=1.5 Hz, 1H), 7.49-7.20 (m, 10H), 6.26 (dd, J=7.8, 2.7 Hz, 1H), 6.11 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.46 (d, J=6.0 Hz, 2H); MS (ES+) m/z 417.2 (M+1).

Provenance & Evidence