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

HRID 36103Notes

Reaction equation

HRID 36103 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, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of crude methyl 3-benzyl-2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate (0.75 g) in MeOH (30 mL) and conc. aqueous HCl (1 mL) and 100 mg of moist Pearlman's catalyst were shaken under 1 atm. H2 for 24 h. Filtration, concentration, and extraction from dilute NH4OH with EtOAc followed by drying (Na2SO4), concentration, and purification (SiO2, 5% MeOH/EtOAc) gave methyl 2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate as a solid.

Workup

  1. filtrationFiltration, concentration, and extraction from dilute NH4OH with EtOAc
  2. customby drying
  3. concentration(Na2SO4), concentration, and purification (SiO2, 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-63f3a423cae34e24b751bf500afa0ad7
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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