Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | HCID 131729969 | HCID 131729969 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15555103 | HCID 15555103 | 67% |
Reaction Steps
To the mixture of sodium (((3-bromo-2-naphthyl)methoxy)methyl)trifluoroborate (30 mg, 0.088 mmol) synthesized in Example 6 and 1,4-dioxane (1.0 ml), water (0.15 ml), cesium carbonate (86 mg, 0.26 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (7.2 mg, 0.018 mmol), palladium(II) acetate (2.0 mg, 0.009 mmol) were added at room temperature, and the obtained reaction mixture was then stirred at 100° C. (an outer temperature) for 16 hours. The reaction mixture was cooled to room temperature, and then water and dichloromethane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1), thereby obtaining the entitled compound (10 mg, 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273885B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-2a105c7927bc46ff9ee7cfc72f8567a2 |
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| Source note | uspto-grants-2012_09 |
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