(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate → Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

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Reaction Steps

A mixture of (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate (0.427 g, 1.615 mmol), (2-amino-5-fluorophenyl)(pyridin-2-yl)methanone (0.384 g, 1.777 mmol), and sodium tetrachloroaurate(III) dihydrate (0.032 g, 0.081 mmol) in 2-propanol (9.50 mL) was heated under reflux. After 71 h, the mixture was cooled to rt and evaporated to dryness. The mixture was dissolved in DCM (50 mL) and washed with brine (1×50 mL), and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.423 g, 0.952 mmol, 58.9% yield) as orange syrupy solid: LC-MS (ESI) m/z 445.1 [M+H]+. The orange syrupy solid was used without further purification. Epimerization occurred during the condensation.

Provenance & Evidence