Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | HCID 67504974 | HCID 67504974 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67505374 | HCID 67505374 | 68.7% |
Reaction Steps
3-Bromo-5-methyl-2-phenoxy-pyridine (0.79 g, 3.0 mmol) was dissolved in toluene (5 mL). To this solution was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloro-methane complex (120 mg), 4-chlorophenyl-boronic acid (0.7 g, 4.5 mmol), and 2 N sodium carbonate solution (4.7 mL). The whole mixture was heated with stirring at 90° C. for 18 h, cooled to room temperature and eluted with ethyl acetate over 10 g ChemElut (Varian). The solvent was evaporated and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 0.61 g of the title compound as a yellowish oil, MS (ISP) 296.4 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188093B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-513ddd7f879148c79b3d3d34227a6ff1 |
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| Source note | uspto-grants-2012_05 |
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