Dimethylformamide → 3-(3,4-Dimethyl-benzoyl)-1-(3-fluoro-pyridin-2-ylmethyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4ll was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 138.6 mg (0.50 mmol) of 3-(3,4-Dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 123.5 mg (0.65 mmol) of 2-bromomethyl-3-fluoro-pyridine. The crude product was purified by flash chromatography to yield 96 mg of 4ll as a colorless solid: LC-MSD, m/z for C24H19FN2O2, [M+H]+=387.5, [M+2H]+=388.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.192 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 5.56 (s, 2H), 7.17 (d, 1H), 7.31 (m, 1H), 7.38 (t, 1H), 7.46 (t, 1H), 7.56-7.70 (m, 4H), 8.35-8.42 (m, 2H), 8.42-8.47 (m, 1H).

Provenance & Evidence