Sodium hydride → HCID 16730852, compound

Participants

Reaction Steps

Compound 4v was prepared following the procedure outlined in Step 3 of Example 1 using 10.4 mg (0.26 mmol) of sodium hydride (60%), 71 mg (0.20 mmol) of 7-(3,4-dimethyl-benzoyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-g]quinolin-8-one, 3 mL of anhydrous dimethylformamide, and 49.1 mg (0.26 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 29 mg of 4v as a colorless solid: Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.922 min; LC-MSD, m/z for C24H18F3NO4, [M+H]+=466.4, [M+2H]+=467.4; 1H NMR (400 MHz, CDCl3/HCl): δ 2.2-2.4 (d, 6H), 5.40 (s, 2H), 7.02-7.10 (m, 2H), 7.12-7.22 (m, 3H), 7.34-7.42 (m, 1H), 7.52-7.57 (d, 1H), 7.62 (s, 1H), 8.10 (s, 1H), 8.24 (s, 1H).

Provenance & Evidence