Methyl 3-benzyl-2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate → HCID 178437553, compound

HRID 2399526Notes

Reaction equation

HRID 2399526 reaction equation
C([N:8]1[C:12]2=[N:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=[C:9]1[CH2:22][CH3:23])C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[CH2:22]([C:9]1[N:8]=[C:12]2[NH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=1)[CH3:23]

Participants

5

Reactant 1

HCID 19385742Methyl 3-benzyl-2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate

Product 1

HCID 178437553HCID 178437553, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 750 mg of the crude product of Step F in MeOH (30 mL), concentrated aqueous HCl (1 mL), and 100 mg of moist Pearlman's catalyst were shaken under 1 atm. H2 for 24 hours. The reaction was incomplete so 100 mg more of the catalyst was added and the reaction was shaken as described above for an additional 24 hours. Filtration, concentration, and extraction from dilute NH4OH with EtOAc followed by drying (Na2SO4), concentration, and purification (SiO2, 5% MeOH/EtOAc) gave 250 mg of the title compound as a solid.

Workup

  1. additionwas added
  2. stirringthe reaction was shaken
  3. customas described above for an additional 24 hours
  4. filtrationFiltration, concentration, and extraction from dilute NH4OH with EtOAc
  5. customby drying
  6. concentration(Na2SO4), concentration, and purification (SiO2, 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-cd78504f5704418893b19f75c0593843
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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