Potassium Carbonate → HCID 22250324, compound

HRID 1391653Notes

Reaction equation

HRID 1391653 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:12][C:13]([F:20])([F:19])[C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([N:16]2[CH:17]=[CH:18][C:14]([C:13]([F:20])([F:19])[F:12])=[N:15]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 22250324HCID 22250324, compoundYield 62.2%

Conditions

Temperature
100 °C

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. 1H NMR (CDCl3) δ 6.75 (m, 1H), 7.5 (m, 1H), 8.2 (m, 2H), 8.7 (m, 1H).

Workup

  1. customThe cooled reaction mixture
  2. extractionThe mixture was extracted twice with ether (100 mL)
  3. washthe combined ether extracts were washed twice with water (100 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-abf1217d36ae42508e8c059885a464f0
Source dataset
uspto-grants-2008_03
Patent number
US07338978B2

Reaction notes

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