Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate | HCID 11514385 | — |
| Reactant | HCID 57704617 | HCID 57704617 | — |
| Catalyst | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57704605 | HCID 57704605 | 79.2% |
Reaction Steps
Compound 30-2 (9.48 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (7.34 g) synthesized by a known method (for example, Tetrahedron vol. 57 (2001) 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (868 mg), bis(acetonitrile)palladium(II) dichloride (157 mg) and cesium carbonate (25.6 g) in acetonitrile (200 ml) were stirred at 80° C. for 8 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object product (11.1 g) as a pale-brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809304B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-9eb51cd5c90e40c79a423f76984d0dd4 |
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| Source note | uspto-grants-2014_08 |
|---|