Reaktion #502096

ord-6dbb113b7c624b0eb8697d1e79e11c69

Reaktionsgleichung

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
Ausbeute 38.2%
O=Cc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde
Ausbeute 38.2%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedegassed with argon
  2. 2
    Sonstigeirradiated at 90° C. for 30 min
  3. 3
    TemperaturAfter cooling
  4. 4
    Sonstigethe catalyst is removed by filtration
  5. 5
    Waschenwashed with ethyl acetate
  6. 6
    SonstigeThe organic phase is separated
  7. 7
    Sonstigedried
  8. 8
    Einengenthe filtrate is concentrated under reduced pressure
  9. 9
    SonstigeThe residue is purified by silica gel chromatography, elution

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088765B2uspto-grants-2012_01