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

Beteiligte Stoffe

Reaktionsschritte

Compound 4t 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 3e, 3 mL of anhydrous dimethylformamide, 75.6 mg (0.40 mmol) of 3-methylbenzylbromide. The crude product 4t was purified by flash chromatography to yield 45 mg of colorless solid: LC-MSD, m/z for C24H19NO2, [M+H]+=354.4, [M+2H]+=355.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.146 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.35 (s, 3H), 5.38 (s, 2H), 7.00 (d, 2H), 7.33 (d, 1H), 7.22-7.26 (m, 1H), 7.36-7.45 (m, 4H), 7.50-7.60 (m, 2H), 7.82-7.86 (m, 2H), 8.31 (s, 1H), 8.44-8.48 (m, 1H).

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