Sodium hydride → 3-(3-Methyl-benzoyl)-1-pyridin-2-ylmethyl-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4w was prepared following the procedure outlined in Step 3 of Example 1 using 52 mg (1.3 mmol) of sodium hydride (60%), 132 mg (0.5 mmol) of 3-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3g, 3 mL of anhydrous dimethylformamide, and 164 mg (0.65 mmol) of 2-bromomethylpyridine hydrobromide. The crude product was purified by flash chromatography to yield 55 mg of a pale yellow solid 4w: Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.913 min; LC-MSD, m/z for C23H18N2O2, [M+H]+=355.4, [M+2H]+=356.4; 1H NMR (400 MHz, CDCl3/HCl): δ 2.40 (s, 3H), 5.50 (s, 2H), 7.12 (d, 1H), 7.22-7.35 (m, 3H), 7.38-7.46 (m, 2H), 7.56-7.68 (m, 4H), 8.56 (s, 1H), 8.46 (d, 1H), 8.62 (d, 1H).

Provenance & Evidence