Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | 3-Bromo-5-(difluoromethoxy)pyridine | HCID 59108568 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 64204670 | HCID 64204670 | 72.2% |
Reaction Steps
3-Bromo-5-(difluoromethoxy)pyridine (813 mg, 3.63 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.84 g, 7.25 mmol), potassium acetate (1.07 g, 11 mmol), and bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (296 mg, 0.36 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (201 mg, 0.36 mmol) were suspended in dioxane (35 ml) and stirred at 90° C. overnight. After usual work-up with water and ethyl acetate, the reaction crude was purified by reverse phase chromatography (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give 495 mg (72% yield) of the title compound as a yellow oil. Purity 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09388189B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-d502da218988450bbea55c4306430304 |
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| Source note | uspto-grants-2016_07 |
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