Dimethylformamide → 3-(3,4-Dimethyl-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4z was prepared following the procedure outlined in Step 3 of Example 1 using 15.6 mg (0.39 mmol) of sodium hydride (60%), 83.2 mg (0.30 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 73.0 mg (0.39 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 61 mg of a colorless solid 4z: LC-MSD, M/z for C25H22N2O2, [M+H]+=383.4, [M+2H]+=384.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.484 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.32 (d, 6H), 2.58 (s, 3H), 5.42 (s, 2H), 6.83 (d, 1H), 7.08 (d, 1H), 7.16 (d, 1H), 7.36-7.43 (m, 2H), 7.48-7.60 (m, 3H), 7.64 (s, 1H), 8.31 (s, 1H), 8.46 (d, 1H).

Provenance & Evidence