反应详情

温度

100 °C

A mixture of methyl cis-(1aRS,7bSR)-5-(2-bromo-4-fluorobenzenesulfonylmethyl)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 5, 0.66 g), N,N-diethyl-N—((Z)-1-tributylstannanylprop-1-en-3-yl)amine (Intermediate 2, 1.17 g), tri-tert-butylphosphonium tetrafluoroborate (0.145 g), Iris-(dibenzylideneacetone)-dipalladium (0.066 g) in dioxane (16 mL) and DMSO (1.6 mL) was degassed and purged with nitrogen, then heated at 100° C. for 1.5 hours. After cooling, the mixture was poured into brine and extracted with ethyl acetate. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-15% to give methyl cis-(1aRS,7bSR)-5-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.72 g) as a glass.

1. customDMSO (1.6 mL) was degassed
2. custompurged with nitrogen
3. temperatureAfter cooling
4. additionthe mixture was poured into brine
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. customThe filtrate was evaporated to dryness
9. customthe residue was purified by chromatography on silica
10. washeluting with a mixture of methanol and DCM with a gradient of 0-15%