2-Hydroxyquinoline → HCID 69737188, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-hydroxy-1-(2,2,2-trifluoroethyl)-1H-quinolin-2-one (0.996 g, 3.6 mmol) was suspended in dry acetonitrile (50 mL) under argon and treated with sodium hydride (0.16 g, 60% wt in mineral oil, 4 mmol). After stirring for 10 minutes, 1,1,1-trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (1.36 g, 3.8 mmol) was added and the mixture heated to 50° C. for 6 hours. Analysis by LC/MS indicated the starting quinolone had been completely consumed and 4-aminopiperidine-1-carboxylic acid ethyl ester (770 μL, 4.5 mmol) was added. The reaction was heated to reflux for 18 hours at which time LC/MS analysis indicated complete consumption of the intermediate triflate. The solution was diluted with ethyl acetate and washed with 1 N NaOH. The organic layer was dried with sodium sulfate and concentrated under reduced pressure to give the crude product. This material was purified by silica chromatography using DCM and methanol eluent gave the title compound (0.91 g). 1H NMR (300 MHz, CDCl3) δ ppm 1.31 (5H, t, J=7.03 Hz), 2.02 (2H, m), 2.85 (2H, m), 3.50 (1H, m), 4.05 (2H, q, J=7.02 Hz), 4.80-5.11 (4H, m), 5.78 (1H, s), 7.28 (2H, m), 7.52 (2H, m).

Provenance & Evidence