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

Participants

Reaction Steps

A solution of (2-amino-5-fluorophenyl)(3-methylpyridin-2-yl)methanone (0.29 g, 1.26 mmol), (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate (0.366 g, 1.386 mmol), and sodium tetrachloroaurate(iii) dihydrate (0.025 g, 0.063 mmol) in 2-propanol (5.0 mL) was stirred at 80° C. for 24 h under an argon atmosphere, then at room temperature for an additional 48 h. The solution was purified by silica gel column chromatography eluting with a gradient of 10-40% EtOAc in hexane to afford tert-butyl 1-(6-fluoro-4-(3-methylpyridin-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate as a dark solid: LC-MS (ESI) m/z 459.2 [M+H]+.

Provenance & Evidence