Cesium carbonate → 1H-Imidazole, 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-

HRID 1803153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803153
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1F.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:9]2[C:10]([O:17][CH3:18])=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[F:7])[CH:6]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 66859027HCID 66859027, VerbindungHCID 178478287HCID 178478287, Verbindung

Produkt 1

HCID 668581431H-Imidazole, 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-Ausbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Step M (5): A mixture of 4-chloro-1H-imidazole (102 mg, 1.00 mmol), 1,2-difluoro-3-methoxy-5-nitrobenzene (200 mg, 1.00 mmol), and cesium carbonate (325 mg, 1 mmol) in acetonitrile (6 mL) was heated at 80° C. for 12 h. The reaction mixture was quenched with 1 N HCl. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (20% EtOAc/hexane) to afford 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-1H-imidazole (60 mg, 22% yield).

Aufarbeitung

  1. customThe reaction mixture was quenched with 1 N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-15fbd86ae2dc41fd9597c307c7b87f66
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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