8-Hydroxyquinoline → HCID 24985793, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-bromo-4-methylthiazole-5-carboxylate (0.50 g, 2.00 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 4-phenylpyridin-2-ol (0.31 g, 1.80 mmol), copper(I) iodide (0.053 g, 0.28 mmol), 8-hydroxyquinoline (0.041 g, 0.28 mmol), and potassium carbonate (0.39 g, 2.80 mmol). The mixture was degassed and the flask was filled with nitrogen. The reaction mixture was heated at 100° C. for 6 hours and then diluted with ethyl acetate (25 mL), washed with 14% aqueous ammonium hydroxide (2×7 mL) and brine (7 mL). The organic layer was dried over anhydrous sodium sulfate, filtered concentrated in vacuo to afford as a yellowish solid (0.45 g, 66%): 1H NMR (300 MHz, DMSO-d6) δ 8.83-8.75 (m, 1H), 7.88-7.81 (m, 2H), 7.60-7.50 (m, 3H), 7.14-7.03 (m, 2H), 4.26 (q, J=7.0 Hz, 2H), 2.64 (s, 3H), 1.28 (t, J=7.0 Hz, 3H); MS (ES+) m/z 341.6 (M+1).

Provenance & Evidence