HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium Carbonate → 2-Fluoro-3-(2-methylpyridin-4-yl)pyridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 3-Bromo-2-fluoropyridine | HCID 2762778 | — |
| Edukt | 2-Methylpyridine-4-boronic acid | HCID 4192664 | — |
| Edukt | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Katalysator | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Lösungsmittel | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Produkt | 2-Fluoro-3-(2-methylpyridin-4-yl)pyridine | HCID 58548572 | — |
Reaktionsschritte
To a round bottomed flask was added 3-bromo-2-fluoropyridine (1.0376 g, 5.9 mmol), 2-methylpyridin-4-ylboronic acid (1.6154 g, 12 mmol), tris(dibenzylideneacetone)dipalladium(o) (0.5501 g, 0.59 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.4846 g, 1.2 mmol), and sodium carbonate (0.74 mL, 18 mmol) in acetonitrile:water (5:1 ratio) at 85° C. to stir overnight. The reaction was monitored by LCMS. Upon completion, the solvents were evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (40S), eluting with a gradient of 0.5% to 5% methanol in DCM, to provide 4-(2-fluoropyridin-3-yl)-2-methylpyridine. [M+1]=189.0.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08759532B2 |
| Quelldatensatz | uspto-grants-2014_06 |
| ORD ID | ord-85ea96b7b6244ba8b2f8b4b4153016ce |
| Quellennotiz | uspto-grants-2014_06 |