Reaction #792153

ord-b43775164adb4ab08be9ccdf83415156

Reaction equation

FC(F)(F)c1cccnc1Cl
2-chloro-3-trifluoromethylpyridine
FC(F)(F)c1cc[nH]n1
3-trifluoromethylpyrazole
O=C([O-])[O-].[K+].[K+]
potassium carbonate
FC(F)(F)c1ccn(-c2ncccc2C(F)(F)F)n1
title compound
Yield 62.2%
FC(F)(F)c1ccn(-c2ncccc2C(F)(F)F)n1
3-Trifluoromethyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine
Yield 62.2%

Solvents

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe cooled reaction mixture
  2. 2
    ExtractionThe mixture was extracted twice with ether (100 mL)
  3. 3
    Washthe combined ether extracts were washed twice with water (100 mL)
  4. 4
    DryingThe organic layer was dried with magnesium sulfate
  5. 5
    Concentrationconcentrated to an oil

Procedure

A mixture of 2-chloro-3-trifluoromethylpyridine (3.62 g., 21 mmol), 3-trifluoromethylpyrazole (2.7 g., 20 mmol), and potassium carbonate (6.0 g, 43 mmol) were heated at 100° C. for 18 h. The cooled reaction mixture was added to ice/water (100 mL). The mixture was extracted twice with ether (100 mL) and the combined ether extracts were washed twice with water (100 mL). The organic layer was dried with magnesium sulfate and concentrated to an oil. Chromatography on silica gel with hexanes:ethyl acetate 8:1 to 4:1 as eluent gave the title compound (3.5 g) as an oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09173400B2uspto-grants-2015_11