Selectfluor → HCID 22341791, compound

Participants

Reaction Conditions

Reaction Steps

3-(5-{[4-(methylsulfonyl)piperazin-1-yl]methyl}-1H-indol-2-yl)quinolin-2(1H)-one (3-1, 60 mg, 1.37 mmol) was dissolved in 5 mL of anhydrous dimethylsolfoxide and diluted with 5 mL of anhydrous acetonitrile. The solution was cooled to 0° C., and the fluorinating reagent, 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate, 3-2 (0.25 equiv., 12 mg, 0.03 mmol) was added. After addition, the ice bath was removed, and the reaction stirred at room temperature for 30 minutes. 3-2 was continually added in this fashion until half of the starting material was consumed. At which point, the reaction was diluted with ethyl acetate (150 mL) and partitioned with water (25 mL). The two layers were separated, and the organic layer was washed several times with water. The organic layer was condensed under vacuum. The crude residue was purified by reverse phase HPLC (5-95% ACN/H2O-40 minutes). The pure fractions were combined and volatiles were removed under reduced pressure. The resulting solution was partitioned with ethyl acetate (200 mL) and washed with 1 N NaOH (15 mL) and brine. The organic layer was dried with Na2SO4, filtered and condensed under vacuum. The resulting pure product was isolated as yellow solid; 1H NMR (500 MHz, DMSO-d6) δ 12.3 (s, 1H), 11.3 (s, 1H), 8.47 (s, 1H), 7.83 (d, 1H, J=7.8 Hz), 7.58-7.52 (m, 2H), 7.46 (s, 1H), 7.39 (d, 1H, J=8.3 Hz), 7.26 (t, 1H, J=7.8 Hz), 7.13 (d, 1H, J=8.5 Hz), 3.60 (s, H), 3.11 (m, 4H), 2.87 (s, 3H), 2.48 (m, 4H).

Provenance & Evidence