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

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Reaction Steps

Compound 4p was prepared following the procedure outlined in Step 3 of Example 1 using 32 mg (0.8 mmol) of sodium hydride (60%), 86 mg (0.31 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 101.2 mg (0.40 mmol) of 4-bromomethylpyridine hydrobromide. The crude product was purified by flash chromatography to yield 27 mg of yellowish solid 4p: LC-MSD, m/z for C24H20N2O2, [M+H]+=369.4, [M+2H]+=370.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.334 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 5.4 (s, 2H), 7.10 (d, 1H), 7.16-7.22 (m, 2H), 7.42 (t, 1H), 7.52-7.66 (m, 3H), 8.26 (d, 1H), 8.48 (m, 1H), 8.58-8.64 (m, 2H).

Provenance & Evidence