反应详情

温度

90 °C

1,1-Dimethylethyl[(5-bromo-2,3-dichlorophenyl)methyl]cyclopropylcarbamate (1 eq.) from the previous step and 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in a 2:1 (v/v) mixture of DMF:n-PrOH (0.1 M). To this solution was then added palladium(II) acetate (0.05 eq.) and triphenylphosphine (0.15 eq.) before the vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 N aq. Na2CO3 (2 eq.) was added and the resulting biphasic suspension was heated at 90° C. for 18 h. The now black suspension was cooled to RT, diluted with water and extracted with 1:1 (v/v) hexanes:ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→9:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

1. additionback-filled with nitrogen
2. temperatureThe now black suspension was cooled to RT
3. extractionextracted with 1:1 (v/v) hexanes
4. washThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
5. dry with materialThis was then dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate concentrated in vacuo
8. customto afford a pale yellow oil
9. customPurification of the crude product
10. customthus obtained by way of flash chromatography (SiO2, Hex→9:1 (v/v) Hex:EtOAc)