反应详情

温度

100 °C

To a 4:1 (v/v) DMF:n-propanol solution (0.15 M) of N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (2 eq.) was added trans-dibromobis(triphenylphosphine) palladium(II) (0.05 eq.) followed by sodium carbonate (2 M aqueous solution, 3 eq.). The reaction vessel was evacuated and purged with nitrogen five times and then heated at 100° C. for 2 h. The cooled reaction mixture was poured into aq. sat. NH4Cl and then extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:7 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as an oil.

1. customThe reaction vessel was evacuated
2. custompurged with nitrogen five times
3. customThe cooled reaction mixture
4. extractionextracted with EtOAc
5. washThe combined organic extracts were washed further with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customPurification of the crude product
10. customthus obtained by way of flash chromatography (SiO2, 3:7 (v/v) Hex:EtOAc→EtOAc)