Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloro-6-(trifluoromethyl)pyridine | HCID 602334 | — |
| Reactant | Bis(adamantan-1-yl)(butyl)phosphane | HCID 11371790 | — |
| Reactant | Potassium ethyl(trifluoro)borate(1-) | HCID 23668491 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59218701 | HCID 59218701 | — |
Reaction Steps
2-Chloro-6-trifluoromethylpyridine (451 mg, 2.5 mmol), ethyltrifluoroborate potassium salt (374 mg, 2.75 mmol), palladium acetate (11 mg, 0.05 mmol), di(1-adamantyl)-n-butylphosphine (27 mg, 0.075 mmol), and cesium carbonate (2.4 g, 7.5 mmol) were suspended in a mixture of toluene and water (10:1, 10 mL). After flushing the vessel under a stream of nitrogen gas for 5 minutes, the reaction tube was sealed and then heated at 100° C. for 18 hours. On cooling, the mixture was partitioned between DCM (15 mL) and water (15 mL). The separated aqueous phase was extracted with DCM (2×15 mL) and the combined organic phases were passed through a phase separator and concentrated in vacuo, affording a yellow oil which was used without further purification (460 mg, crude)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809525B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-1ee8eea76a604003bab5c7db0be92038 |
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| Source note | uspto-grants-2014_08 |
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