Reacción #531813

ord-7828509d36134cdb89b22cfb65774069

Ecuación de reacción

Clc1cccnc1Cl
2,3-dichloropyridine
FC(F)(F)c1cc[nH]n1
3-(trifluoromethyl)-pyrazole
O=C([O-])[O-].[K+].[K+]
potassium carbonate
FC(F)(F)c1ccn(-c2ncccc2Cl)n1
desired intermediate
Rendimiento 75.1%
FC(F)(F)c1ccn(-c2ncccc2Cl)n1
3-chloro-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine
Rendimiento 75.1%

Condiciones de reacción

Temperatura
117.5°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction was cooled to 100° C.
  2. 2
    Filtraciónfiltered through Celite® diatomaceous filter aid
  3. 3
    Otroto remove solids
  4. 4
    OtroN,N-Dimethylformamide and excess dichloropyridine were removed by distillation at atmospheric pressure
  5. 5
    workup.DISTILLATIONDistillation of the product at reduced pressure (b.p. 139-141° C., 7 mm)

Procedimiento

To a mixture of 2,3-dichloropyridine (99.0 g, 0.67 mol) and 3-(trifluoromethyl)-pyrazole (83 g, 0.61 mol) in dry N,N-dimethylformamide (300 mL) was added potassium carbonate (166.0 g, 1.2 mol) and the reaction was then heated to 110-125° C. over 48 hours. The reaction was cooled to 100° C. and filtered through Celite® diatomaceous filter aid to remove solids. N,N-Dimethylformamide and excess dichloropyridine were removed by distillation at atmospheric pressure. Distillation of the product at reduced pressure (b.p. 139-141° C., 7 mm) afforded 113.4 g of the desired intermediate as a clear yellow oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08475819B2uspto-grants-2013_07