Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Cyanophenol | HCID 13394 | — |
| Reactant | 2-Bromo-3-methoxypyridine | HCID 90364 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23506255 | HCID 23506255 | 72.2% |
Reaction Steps
2-Bromo-3-methoxypyridine (15 g, 68 mmol) and 3-cyanophenol (8.9 g, 75 mmol) are dissolved in DMF (150 ml), and thereto are added potassium carbonate (28 g, 0.2 mol) and cuprous bromide (10.7 g, 75 mmol), and the mixture is heated under reflux at 140° C. for 1.5 hours. After being allowed to cool, to the reaction solution is added ethyl acetate (1000 ml), and the mixture is washed with a saturated brine (200 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from isopropyl ether/hexane to give the title compound (11.1 g) as pale brown crystals, m.p. 88-89° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06555557B1 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-92ab59c4abc44fab8753728359b6a202 |
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| Source note | uspto-grants-2003_04 |
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