Reacción #325553

ord-325bb98fb8fd415ea261e8d718bd0fed

Ecuación de reacción

Cn1nccc1-c1cn[nH]c1
2-methyl-1′H,2H-3,4′-bipyrazole
FC(F)(F)c1ccc(I)cc1
4-iodobenzotrifluoride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN[C@@H]1CCCC[C@H]1NC
trans-N,N′-dimethylcyclohexan-1,2-diamine
[Cl-].[NH4+]
ammonium chloride
Cn1nccc1-c1cnn(-c2ccc(C(F)(F)F)cc2)c1
title compound
Rendimiento 80.7%
Cn1nccc1-c1cnn(-c2ccc(C(F)(F)F)cc2)c1
2-Methyl-1′-[4-(trifluoromethyl)phenyl]-1′H,2H-3,4′-bipyrazole
Rendimiento 80.7%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe obtained mixture was then extracted with chloroform
  2. 2
    SecadoThe organic layer was dried over anhydrous magnesium sulfate
  3. 3
    Concentraciónwas then concentrated under a reduced pressure
  4. 4
    OtroThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to 1:1)

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08642626B2uspto-grants-2014_02