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 131729970 | HCID 131729970 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22959423 | HCID 22959423 | 4% |
Reaction Steps
To the mixture of sodium (((2,4-dichlorobenzyl)oxy)methyl)trifluoroborate (50 mg, 0.18 mmol) synthesized in Example 8 and 1,4-dioxane (1.5 ml), water (0.15 ml), cesium carbonate (170 mg, 0.53 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (15 mg, 0.036 mmol), and palladium(II) acetate (4.0 mg, 0.018 mmol) were added at room temperature, and the obtained reaction mixture was then stirred at 100° C. (an outer temperature) for 8.5 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 (1.1 mg, 4%).
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-300cd4a73cf344c5ba39d72f697a1ee6 |
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| Source note | uspto-grants-2012_09 |
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