HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3-Methyl-1-hexyn-3-ol → rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 3-Methyl-1-hexyn-3-ol | HCID 20347 | — |
| Edukt | HCID 23683387 | HCID 23683387 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Produkt | rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 9884773 | — |
Reaktionsschritte
Using Method D above, 3-methyl-1-hexyn-3-ol (98 mg, 0.87 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material I supra) (127 mg, 0.4 mmol) using (Ph3P)2PdCl2 (46 mg) and CuI (22 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 22 h yielding rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 92 mg, 66%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06303793B1 |
| Quelldatensatz | uspto-grants-2001_10 |
| ORD ID | ord-473317c3165c4675a0b1426ebcddaee8 |
| Quellennotiz | uspto-grants-2001_10 |