2-Hydroxyquinoline → HCID 69738349, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-hydroxy-1-pyridin-4-ylmethyl-1H-quinolin-2-one (0.891 g, 3.1 mmol) was suspended in dry acetonitrile (50 mL) under argon and treated with sodium hydride (0.14 g, 60% wt in mineral oil, 3.5 mmol). After stirring for 10 minutes, 1,1,1-trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (1.18 g, 3.3 mmol) was added and the mixture heated to 50° C. for 1 hour. Analysis by LC/MS indicated the starting quinolone had been completely consumed and the reaction was transferred to a pressure vessel containing 4-aminopiperidine-1-carboxylic acid t-butyl ester (0.80 g, 4 mmol). The pressure vessel was sealed and heated to 100° C. for 7 hours. After cooling, the solution was diluted with ethyl acetate, washed with 1N NaOH, and dried with sodium sulfate before concentrating to give the crude product. Purification by silica chromatography using DCM and methanol eluent gave the title compound (1.22 g). 1H NMR (300 MHz, CDCl3) δ ppm 1.41 (11H, m), 2.03 (2H, m), 2.83 (2H, m), 3.50 (1H, m), 4.05 (2H, m), 5.39 (3H, m), 5.77 (1H, s), 6.87 (1H, d, J=9.04 Hz), 6.90 (2H, m), 7.23 (1H, m), 7.66 (1H, m), 8.40 (2H, m).

Provenance & Evidence