HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Chloride → 5-(6-Bromo-2-pyridyl)-4-pentynoic acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Chloride | HCID 312 | — |
| Edukt | 2,6-Dibromopyridine | HCID 12274 | — |
| Edukt | 2-Pentynoic acid, methyl ester | HCID 90470 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Produkt | 5-(6-Bromo-2-pyridyl)-4-pentynoic acid methyl ester | HCID 15661798 | 43,3% |
Reaktionsschritte
A solution of 4.73 g of 2,6-dibromopyridine in 150 ml of triethylamine is mixed under ice cooling with 2.69 g of pentynoic acid methyl ester, 350 mg of bis-triphenylphosphinepalladium(II) chloride and 48 mg of copper(I) iodide and the mixture is stirred for 1 hour. Then, the ice bath is removed and it is stirred for 3 hours at room temperature. The precipitate--consisting of 2,6-bis-(4-methoxycarbonyl-1-butinyl)-pyridine and triethylammonium bromide--is suctioned off and the filtrate is evaporated to dryness. The residue is chromatographed on silica gel with hexane/ethyl acetate=95/5 to 75/25. 2.32 g of 5-(6-bromo-2-pyridyl)-4-pentynoic acid methyl ester of melting point 59°-61° C. is obtained.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05614634 |
| Quelldatensatz | uspto-grants-1997_03 |
| ORD ID | ord-f26ab3145d8d4fd990174786fecc2399 |
| Quellennotiz | uspto-grants-1997_03 |