Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4xx was prepared following the procedure described in Step 3 of Example 1 using 55 mg (0.20 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 10 mg (0.26 mmol) of 60% sodium hydride and 62 mg (0.26 mmol) of 2-bromomethyl-6-trifluoromethyl-pyridine, and 1.7 mL N,N-dimethylformamide and stirring the reaction mixture for 6 h at rt. The crude product was purified by flash chromatography using 20-75% ethyl acetate in hexane yielded to provide 45 mg of the product as white solid: LC-MSD, m/z for C25H19F3N2O2 [M+H]+: 437.3; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time=2.8 min; 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H), 2.3 (s, 3H), 5.6 (s, 2H), 7.1-7.2 (m, 1H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 2H), 7.5-7.65 (m, 15 4H), 7.8-7.9 (m, 1H), 8.35 (s, 1H), 8.4-8.5 (m, 1H).

Provenance & Evidence