Reacción #502096

ord-6dbb113b7c624b0eb8697d1e79e11c69

Ecuación de reacción

Clc1ccc(-c2cn3cc(I)ccc3n2)cc1
2-(4-chlorophenyl)-6-iodoimidazo[1,2-a]pyridine
O=Cc1ccc(B(O)O)o1
5-formyl-2-furanboronic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCO
ethanol
O=Cc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
compound
Rendimiento 38.2%
O=Cc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde
Rendimiento 38.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrodegassed with argon
  2. 2
    Otroirradiated at 90° C. for 30 min
  3. 3
    TemperaturaAfter cooling
  4. 4
    Otrothe catalyst is removed by filtration
  5. 5
    Lavadowashed with ethyl acetate
  6. 6
    OtroThe organic phase is separated
  7. 7
    Otrodried
  8. 8
    Concentraciónthe filtrate is concentrated under reduced pressure
  9. 9
    OtroThe residue is purified by silica gel chromatography, elution

Procedimiento

300 mg of 2-(4-chlorophenyl)-6-iodoimidazo[1,2-a]pyridine, 118 mg of 5-formyl-2-furanboronic acid, 89 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, 280 mg of potassium carbonate, 1.5 ml of ethanol and 1 ml of water are placed in a microwave tube and degassed with argon. The tube is placed in a microwave apparatus and irradiated at 90° C. for 30 min. After cooling, the catalyst is removed by filtration and washed with ethyl acetate. The organic phase is separated and dried and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 104 mg of compound are obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08088765B2uspto-grants-2012_01