Reacción #1005972

ord-25c05e8c18f04a95a89c7395fd3483c1

Ecuación de reacción

CCS(=O)(=O)c1ccccc1C(=O)CBr
2-bromo-2′-ethylsulfonylacetophenone
Nc1cc(C(F)(F)F)ccn1
2-amino-4-trifluoromethylpyridine
CCS(=O)(=O)c1ccccc1-c1cn2ccc(C(F)(F)F)cc2n1
2-(2-ethylsulfonylphenyl)-7-trifluoromethyl-imidazo[1,2-a]pyridine
Rendimiento 26.0%

Disolventes

Condiciones de reacción

Temperatura
130°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas refluxed for 1 hour
  2. 2
    Concentraciónconcentrated under reduced pressure
  3. 3
    workup.ADDITIONA mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF
  4. 4
    workup.ADDITIONWater was poured to the cooled reaction mixture
  5. 5
    Extracciónthe mixture was extracted with ethyl acetate
  6. 6
    LavadoThe organic layer was washed with water
  7. 7
    Secadodried over anhydrous magnesium sulfate
  8. 8
    Concentraciónconcentrated under reduced pressure

Procedimiento

A mixture of 1.0 g of 2-bromo-2′-ethylsulfonylacetophenone, 334 mg of 2-amino-4-trifluoromethylpyridine and 4 ml of ethanol was refluxed for 1 hour and concentrated under reduced pressure. A mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF was stirred at 130° C. for 1 hour. Water was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 190 mg of 2-(2-ethylsulfonylphenyl)-7-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 8).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09271500B2uspto-grants-2016_03