Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Reactant | 5-Bromo-2-cyclopropylpyridine | HCID 22317722 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118113230 | HCID 118113230 | 80.3% |
Reaction Steps
A mixture of 3-bromo-6-(cyclopropyl)pyridine (2.00 g), 4-formylphenylboronic acid (1.82 g), palladium(II) acetate (113 mg), tripotassium phosphate (4.50 g) and ethylene glycol (16.8 mL) was stirred at 80° C. for 3 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter the crude product was adsorbed on diatomaceous earth, with the solvent being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-50:50) to give the titled compound as a colorless solid (1.81 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422240B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1d0a9e034b254d8c8bf85c13da673d8e |
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| Source note | uspto-grants-2016_08 |
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