Ethanol → HCID 86651941, compound

HRID 1907347Notes

Reaction equation

HRID 1907347 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.[CH:18]([C:20]1[O:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+].C(O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:23]4[O:24][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=4)=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 1511765HCID 1511765, compoundHCID 27343555-Formylfuran-2-boronic acid

Product 1

HCID 86651941HCID 86651941, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

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.

Workup

  1. customdegassed with argon
  2. customirradiated at 90° C. for 30 min
  3. temperatureAfter cooling
  4. customthe catalyst is removed by filtration
  5. washwashed with ethyl acetate
  6. customThe organic phase is separated
  7. customdried
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-501a090d22ee4ad7a699fc05931ca346
Source dataset
uspto-grants-2013_12
Patent number
US08598166B2

Reaction notes

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