反应详情

A solution of 6-bromo-2-quinolinecarboxaldehyde (18.9 g), 1-decyne (12.2 g) and triethylamine (24.3 g) in dry tetrahydrofuran (300 ml) was chilled to 5° C. and degassed, under nitrogen. bis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which was degassed and stirred under nitrogen at room temperature for 30 mins, and then heated at 40° C. for 19 hrs. The mixture was cooled to room temperature, the precipitate was filtered, and the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel, eluting with heptane to heptane:2% ethyl acetate. The appropriate fractions were collected and evaporated. A 2 g-portion of the residue (23.4 g) was chromatographed, eluting with hexane:dichloromethane/2:1 give 1.3 g (64.0%) of product, mp 46.5°-47.5° C.

1. customdegassed, under nitrogen
2. additionbis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which
3. customwas degassed
4. temperatureheated at 40° C. for 19 hrs
5. temperatureThe mixture was cooled to room temperature
6. filtrationthe precipitate was filtered
7. washthe filter cake was washed with ethyl acetate
8. customthe filtrate was evaporated
9. dissolutionThe residue was dissolved in ethyl acetate
10. washwashed with water and brine
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationthe filtrate was concentrated
14. customThe residue was chromatographed on silica gel
15. washeluting with heptane to heptane
16. customThe appropriate fractions were collected
17. customevaporated
18. customA 2 g-portion of the residue (23.4 g) was chromatographed
19. washeluting with hexane