Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 6-Bromopyridine-2-carbaldehyde | HCID 2757009 | — |
| Reactant | 2,4-Bis(trifluoromethyl)phenylboronic acid | HCID 2782667 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86671318 | HCID 86671318 | — |
Reaction Steps
To a solution of 6-bromopicolinaldehyde (1.00 g, 5.38 mmol) in dioxane (30 mL) at ambient temperature was added 2,4-bis(trifluoromethyl)phenylboronic acid (1.38 g, 5.38 mmol), 2M cesium carbonate (8.0 mL, 16 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.220 g, 0.269 mmol). The mixture was degassed (3× vacuum/purge N2), then heated at 80° C. overnight. The mixture was cooled to room temperature and concentrated and the residue then partitioned between water and CH2Cl2. The organic layer concentrated and purified by chromatography (20% ethyl acetate:hexanes) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09012651B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-a58f63bda49b471fb19ea6b178ef896d |
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| Source note | uspto-grants-2015_04 |
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