Reacción #792181

ord-371274c08704439eae6a0827d3fcb3cb

Ecuación de reacción

[K+].[OH-]
Potassium hydroxide
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
product
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
product
Rendimiento 93.0%
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid
Rendimiento 93.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvent was removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe mixture was dissolved in water (40 mL)
  3. 3
    LavadoThe solution was washed with ethyl acetate (20 mL)
  4. 4
    Extracciónwas extracted with ethyl acetate (3×20 mL)
  5. 5
    OtroThe combined extracts were dried
  6. 6
    Otroevaporated
  7. 7
    Otroto give

Procedimiento

Potassium hydroxide (0.5 g, 85%, 2.28 mmol) in water (1 mL) was added to ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (i.e. the product of Step D) (0.66 g, 2.07 mmol) in ethanol (3 mL). After about 30 minutes, the solvent was removed under reduced pressure, and the mixture was dissolved in water (40 mL). The solution was washed with ethyl acetate (20 mL). The aqueous layer was acidified with concentrated hydrochloric acid and was extracted with ethyl acetate (3×20 mL). The combined extracts were dried and evaporated to give the product as a solid (0.53 g, 93% yield), m.p. 178-179° C. (after crystallization from hexanes-ethyl acetate).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09173400B2uspto-grants-2015_11