Sodium hydride → 1-(2-Fluoro-benzyl)-3-(3-methyl-benzoyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4x was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 132 mg (0.50 mmol) of 3-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 123 mg (0.65 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 85 mg of a colorless solid 4x: LC-MSD, m/z for C24H18FNO2, [M+H]+=372.4, [M+2H]+=373.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.687 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.40 (s, 3H), 5.42 (s, 2H), 7.02-7.18 (m, 3H), 7.28-7.36 (m, 3H), 7.36-7.42 (m, 2H), 7.58-7.66 (m, 3H), 8.31 (s, 1H), 8.43-8.47 (m, 1H).

Provenance & Evidence