Phenethyl bromide → HCID 16730931, compound

Participants

Reaction Steps

Compound 4aa was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 138.6 mg (0.50 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 120.3 mg (0.65 mmol) of phenethylbromide. The crude product was purified by flash chromatograph to yield 44 mg of a colorless solid 4aa: LC-MSD, m/z for C26H23NO2, [M+H]+=382.5, [M+2H]+=383.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.551 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 3.20 (t, 2H), 4.40 (t, 3H), 7.08 (d, 2H), 7.13 (d, 1H), 7.20-7.32 (m, 3H), 7.38-7.47 (m, 2H), 7.53-7.58 (d, 2H), 7.73 (t, 1H), 7.80 (s, 1H), 8.48 (d, 1H).

Provenance & Evidence