Sodium hydride → 3-Benzoyl-1-[(2-fluorophenyl)methyl]-1,4-dihydroquinolin-4-one

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Reaction Steps

Compound 4u was prepared following the procedure outlined in Step 3 of Example 1 using 16 mg (0.4 mmol) of sodium hydride (60%), 75 mg (0.31 mmol) of 3-benzoyl-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 74 mg (0.40 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 42 mg of a colorless solid 4u: LC-MSD, m/z for C23H16FNO2, [M+H]+=358.4, [M+2H]+=359.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time =2.291 min; 1H NMR (400 MHz, CDCl3/HCl): δ 5.42 (s, 2H), 7.00-7.20 (m, 3H), 7.28-7.46 (m, 5H), 7.51 (t, 1H), 7.61 (t, 1H), 7.78-7.86 (m, 2H), 8.32 (d, 1H), 8.46 (m, 1H).

Provenance & Evidence