反应详情

温度

80 °C

To a 1:1 (v/v) ethanol:toluene solution (0.18 M) of 1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (1 eq.) and 4-pyridinylboronic acid (1.1 eq.) was added sodium carbonate (2 M aq. solution, 2.6 eq.). The suspension was evacuated and back-filled with N2. Finally, tetrakis(triphenylphosphine)palladium(0) (0.04 eq.) was added in one rapid portion and the reaction suspension was heated at 80° C. for 18 h. The reaction was then quenched with sat. aq. NH4Cl and extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 80:20 (v/v) Hex:EtOAc→ EtOAc) afforded the title compound as a golden yellow oil.

1. customThe suspension was evacuated
2. additionback-filled with N2
3. customThe reaction was then quenched with sat. aq. NH4Cl
4. extractionextracted with EtOAc
5. washThe combined organic extracts were washed further with water and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customPurification of the crude product
10. customthus obtained by way of column chromatography (SiO2, 80:20 (v/v) Hex:EtOAc→ EtOAc)