Potassium Carbonate → 2-Methyl-1'-[4-(trifluoromethyl)phenyl]-1'H,2H-3,4'-bipyrazole

HRID 238371Notes

Reaction equation

[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]1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-325bb98fb8fd415ea261e8d718bd0fed
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642626B2

Reaction notes

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