HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
N,N,N',N'-Tetramethylazodicarboxamide → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | N,N,N',N'-Tetramethylazodicarboxamide | HCID 4278 | — |
| Edukt | Tributylphosphine | HCID 13831 | — |
| Edukt | (6-Hydroxy-indol-1-yl)-acetic acid ethyl ester | HCID 68821422 | — |
| Edukt | 4-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]- | HCID 68822690 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester | HCID 68826126 | 33% |
Reaktionsschritte
To an ice cold solution of (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (100 mg, 455 μmol), 5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (111 mg, 455 μmol) and tributylphosphine (160 μl, 546 μmol) in tetrahydrofuran (10 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (94 mg, 546 μmol). The cooling bath was removed and stirring continued for 14 h. The mixture was filtered over celite and the solvent removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 65 mg (150 μmol, 32%) of the title compound as colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07405236B2 |
| Quelldatensatz | uspto-grants-2008_07 |
| ORD ID | ord-4bc37d558c684ffb9b7c36d389bdd448 |
| Quellennotiz | uspto-grants-2008_07 |