HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 70663585, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (4-Fluoro-2-methylphenyl)boronic acid | HCID 2734665 | — |
| Reactant | 4-Chloro-3-nitropyridine | HCID 2735781 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 70663585 | HCID 70663585 | 91.3% |
Reaction Steps
A solution of 4-chloro-3-nitropyridine (2.4 g, 15.1 mmol, CAS RN 13091-23-1), 4-fluoro-2-methylphenylboronic acid (2.8 g, 18.2 mmol, CAS RN 139911-29-8), potassium carbonate (6.28 g, 45.4 mmol) and palladium tetrakis-triphenylphosphine (794 mg, 0.76 mmol, CAS RN 14221-01-3) in dioxane (75 mL) was heated to reflux for 16 hours. After cooling to room temperature, the reaction mixture was filtered through Celite and all volatiles were removed under reduced pressure. Column chromatography on silica gel (20-33% EtOAc in n-hexane) afforded 4-(4-fluoro-2-methylphenyl)-3-nitropyridine as a yellow crystalline solid (3.2 g, 90%) which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987307B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-59a533bbd0ae4de38ecdd7cbf5f90adf |
| Source note | uspto-grants-2015_03 |