Potassium Carbonate → methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate

HRID 1627315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627315
Cl[CH2:2][C:3]1[N:4]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)([CH3:10])[CH3:9])=[CH:6][N:7]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=1[OH:37])[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=1[O:37][CH2:2][C:3]1[N:4]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)([CH3:9])[CH3:10])=[CH:6][N:7]=1)[C:30]([O:32][CH3:33])=[O:31]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 66619271Methyl 3-chloro-5-fluoro-4-hydroxybenzoateHCID 667400042-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

Produkt 1

HCID 66740309methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (154 mg, 0.39 mmol), methyl 3-chloro-5-fluoro-4-hydroxybenzoate (118 mg 0.57 mmol), potassium carbonate (79 mg, 0.57 mmol), and 18-crown-6 (11 mg, 0.04 mmol) in CH3CN (4 mL) was heated 8 h at 60° C. After cooling, the reaction mixture was filtered, combined with water and DCM, and then extracted further with DCM. The combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The material was purified by chromatography (silica, 0-70% EtOAc/Hex) to give methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate as a white solid (150 mg, 68% yield). MS (EI) m/z 567.3 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. extractionextracted further with DCM
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe material was purified by chromatography (silica, 0-70% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-a1236eb5e3804a5cba27a9add9004556
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785488B2

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