Реакция #502096

ord-6dbb113b7c624b0eb8697d1e79e11c69

Уравнение реакции

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

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеdegassed with argon
  2. 2
    Другоеirradiated at 90° C. for 30 min
  3. 3
    ТемператураAfter cooling
  4. 4
    Другоеthe catalyst is removed by filtration
  5. 5
    Промывкаwashed with ethyl acetate
  6. 6
    ДругоеThe organic phase is separated
  7. 7
    Другоеdried
  8. 8
    Концентрированиеthe filtrate is concentrated under reduced pressure
  9. 9
    ДругоеThe residue is purified by silica gel chromatography, elution

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08088765B2uspto-grants-2012_01