Reaction #502096

Reaction equation

2-(4-chlorophenyl)-6-iodoimidazo[1,2-a]pyridine

5-formyl-2-furanboronic acid

potassium carbonate

ethanol

→

compound

Yield 38.2%

5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde

Yield 38.2%

Solvents

water

Conditions

Workup

1. 1
   Otherdegassed with argon
2. 2
   Otherirradiated at 90° C. for 30 min
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe catalyst is removed by filtration
5. 5
   Washwashed with ethyl acetate
6. 6
   OtherThe organic phase is separated
7. 7
   Otherdried
8. 8
   Concentrationthe filtrate is concentrated under reduced pressure
9. 9
   OtherThe residue is purified by silica gel chromatography, elution

Procedure

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.

Source