1,10-Phenanthroline → (4-Imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid

HRID 1010713Notes

Reaction equation

HRID 1010713 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[N:20][C:15]=2[NH:14][CH:13]=1.C(=C/C(/C=C/C1C=CC=CC=1)=O)\C1C=CC=CC=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].CC#N.O.C(O)(C(F)(F)F)=O>C1(C)C(C)=CC=CC=1.[OH-].[Na+]>[N:12]1[C:16]2[C:15](=[N:20][CH:19]=[CH:18][CH:17]=2)[N:14]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)[CH:13]=1

Participants

9

Reactant 6

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1372144-Iodophenylacetic acidHCID 640180(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-oneHCID 22145617Water TFA acetonitrileHCID 178420746HCID 178420746, compound

Product 1

HCID 53213084(4-Imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 400 mg of 4-iodophenylacetic acid, 273 mg of 4-azabenzimidazole, 17.9 mg of trans,trans-dibenzylideneacetone, 303 mg of 1,10-phenanthroline, 19.2 mg of copper (I) trifluoromethanesulfonate benzene complex and 547 mg of Cs2CO3 in 1.5 ml of xylene is stirred for 80 hours at 125° C. The mixture obtained is allowed to cool to rt and concentrated in vacuo. The concentration residue obtained is dissolved in aqueous 1N NaOH solution and extracted with EtOAc. To the aqueous layer aqueous 1N HCl is added in order to obtain an acidic pH and the mixture obtained is extracted with CH2Cl2. The organic phase obtained is dried (Na2SO4), filtered and concentrated. The concentration residue obtained is subjected to reversed phase MPLC(CH3CN/H2O/TFA). (4-Imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid is obtained.

Workup

  1. customThe mixture obtained
  2. temperatureto cool to rt
  3. concentrationconcentrated in vacuo
  4. customThe concentration residue obtained
  5. extractionextracted with EtOAc
  6. additionTo the aqueous layer aqueous 1N HCl is added in order
  7. customto obtain an acidic pH
  8. customthe mixture obtained
  9. extractionis extracted with CH2Cl2
  10. customThe organic phase obtained
  11. dry with materialis dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe concentration residue obtained

Sources & evidence

ORD record
ord-960b5c488a0243388fad3f86c5374a6d
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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