m-Xylyl bromide → 3-(3-Methyl-benzoyl)-1-(3-methyl-benzyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4y 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 120 mg (0.65 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 92 mg of a colorless solid 4y: LC-MSD, m/z for C25H21NO2, [M+H]+=368.5, [M+2H]+=369.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.586 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.37 (s, 3H), 2.42 (s, 3H), 5.39 (s, 2H), 7.01 (d, 2H), 7.15 (d, 1H), 7.22-7.44 (m, 5H), 7.55-7.58 (m, 3H), 8.29 (s, 1H), 8.47 (d, 1H).

Provenance & Evidence