Reaktionsgleichung
N1C=CC=CC=1C1NC2C=CC=CC=2N=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][C:29]=1[O:35][CH3:36]>[Cu]I.CN(C=O)C>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:30][C:29]=1[O:35][CH3:36]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of 2-(2-pyridyl)benzimidazole (287 mg, 1.469 mmol), cesium carbonate (5.98 g, 18.36 mmol), copper(I) iodide (280 mg, 1.469 mmol) and DMF (5 mL) were combined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The slurry was heated at 60° C. for 1 h, followed by addition of imidazole (500 mg, 7.34 mmol) and 1-bromo-4-iodo-2-methoxybenzene (2.3 g, 7.34 mmol). The reaction mixture was heated at 90° C. for 2 days. The reaction mixture was filtered through celite, washed with EtOAc, and concentrated in vacuo. The crude material was purified by silica gel chromotography (10% to 40% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1H-imidazole (1.25 g, MS: 255.2 [M+H+])
Aufarbeitung
- customvial fitted with an N2 inlet and magnetic stir bar
- temperatureThe reaction mixture was heated at 90° C. for 2 days
- filtrationThe reaction mixture was filtered through celite
- washwashed with EtOAc
- concentrationconcentrated in vacuo
- customThe crude material was purified by silica gel chromotography (10% to 40% EtOAc in heptanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-108fc876de8445358445d32e5ff57c25
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729263B2
Verknüpfte Notizen
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