Dimethylformamide → HCID 16731009, compound

Participants

Reaction Steps

Compound 4hh was prepared following the procedure outlined in Step 3 of Example 1 using 16 mg (0.40 mmol) of sodium hydride (60%), 75 mg (0.30 mmol) of 3-(pyridine-3-carbonyl)-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 74.0 mg (0.4 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 35 mg of 4hh as a colorless solid: LC-MSD, m/z for C23H18N2O2, [M+H]+=355.4, [M+2H]+=356.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.710 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.36 (s, 3H), 5.41 (s, 2H), 7.00 (d, 2H), 7.12-7.28 (m, 2H), 7.34-7.45 (m, 3H), 7.60 (m, 1H), 8.09 (m, 1H), 8.42-8.46 (m, 2H), 8.71 (m, 2H), 8.99 (s, 1H).

Provenance & Evidence