Tetrahydrofuran → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-7-fluoro-1H-quinolin-4-one

Participants

Reaction Conditions

Reaction Steps

Compound 4vv was prepared following the procedure described in Step 3 of Example 1 using 0.050 g (0.169 mmol) of 3-(3,4-dimethyl-benzoyl)-7-fluoro-1H-quinolin-4-one 3k, 0.4 mL of potassium hexamethyldisilazide (0.5 M in toluene, 0.203 mmol) and 50.9 mg (0.203 mmol) of 2-bromo-6-bromomethyl-pyridine in 1.5 mL of tetrahydrofuran and heating the reaction solution at 60° C. for 24 h. The crude product was purified by flash chromatography using 10-80% ethyl acetate in hexane to yield 37.8 mg of 3-(3,4-Dimethyl-benzoyl)-7-fluoro-1-(3-methyl-benzyl)-1H-quinolin-4-one 4vv as a white solid: LC-MSD, m/z for C24H18BrFN2O2 [M+H]: 465.4, 466.5, 467.4, 468.4; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time=2.8 min; 1H NMR (400 MHz, CDCl3): δ 8.47 (1H, m), 8.23 (1H, s), 7.64 (1H, s), 7.56 (1H, m), 7.53 (1H, m), 7.47 (1H, m), 7.18 (1H, m), 7.12 (1H, m), 7.05-7.02 (2H, m), 5.39 (2H, s), 2.32 (3H, s), 2.31 (3H, s).

Provenance & Evidence