反应详情

Under a nitrogen atmosphere, pyridine hydrochloride (1.6 g, 14 mmol), trimethyl orthobutyrate (1.62 g, 11.0 mmol), 2-chloro-N4-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}quinoline-3,4-diamine (2.10 g, 5.49 mmol), and toluene (50 mL) were combined and heated at reflux for four hours under a Dean-Stark trap. The volatiles were removed under reduced pressure. The resulting oil was dissolved in ethyl acetate, and the solution was washed sequentially with aqueous potassium carbonate, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 4:6 hexane:ethyl acetate) to provide 1.22 g of 4-chloro-1-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a pale yellow solid.

1. temperatureheated
2. temperatureat reflux for four hours under a Dean-Stark trap
3. customThe volatiles were removed under reduced pressure
4. dissolutionThe resulting oil was dissolved in ethyl acetate
5. washthe solution was washed sequentially with aqueous potassium carbonate, water, and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationand concentrated under reduced pressure
9. customThe crude product was purified by column chromatography on silica gel (eluting with 4:6 hexane:ethyl acetate)