Potassium Carbonate → 2-Methyl-1'-[4-(trifluoromethyl)phenyl]-1'H,2H-3,4'-bipyrazole
Reaktionsgleichung
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][NH:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1.I[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC.[Cl-].[NH4+]>[Cu](I)I.CN(C)C=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:11]=2)=[CH:5][CH:4]=[N:3]1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Under a nitrogen atmosphere, a mixture of 2-methyl-1′H,2H-3,4′-bipyrazole (176 mg), 4-iodobenzotrifluoride (485 mg), copper iodide (45 mg), potassium carbonate (329 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (135 mg) and N,N-dimethylformamide (2.2 mL) was stirred at 100° C. for 16 hours. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to 1:1), so as to obtain the title compound (280 mg) in the form of a colorless solid.
Aufarbeitung
- extractionthe obtained mixture was then extracted with chloroform
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationwas then concentrated under a reduced pressure
- customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to 1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-325bb98fb8fd415ea261e8d718bd0fed
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08642626B2
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