Methanol → Methyl 2-methyl-3h-imidazo[4,5-b]pyridine-5-carboxylate

HRID 1368238Notes

Reaction equation

HRID 1368238 reaction equation
C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:31]1[N:36]=[C:35]2[N:37]=[C:38]([CH3:40])[NH:39][C:34]2=[CH:33][CH:32]=1.CN(C)[CH:43]=[O:44].[C]=O.[CH3:48][OH:49]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH3:40][C:38]1[NH:39][C:34]2[C:35]([N:37]=1)=[N:36][C:31]([C:48]([O:44][CH3:43])=[O:49])=[CH:32][CH:33]=2

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 223879615-bromo-2-methyl-3H-imidazo[4,5-b]pyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 22387777Methyl 2-methyl-3h-imidazo[4,5-b]pyridine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

Palladium acetate (1.18 g), 1,3-bis(diphenylphosphino)propane (2.31 g) and 5-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (3.72 g) were charged in an autoclave, and N,N-dimethylformamide (18.6 ml), methanol (14.9 ml) and triethylamine (5.4 ml) were added. The mixture was stirred at 85° C. for 14 hr in a 10 atm. carbon monoxide atmosphere. The reaction mixture was allowed to cool and the solvent was evaporated. Methanol (60 ml) was added to the residue and heated, and the insoluble matter was filtered off while hot. The filtrate was concentrated to give methyl 2-methyl-1H-imidazo[4,5-b]pyridine-5-carboxylate (2.95 g) as a white powder.

Workup

  1. additionwere added
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. additionMethanol (60 ml) was added to the residue
  5. temperatureheated
  6. filtrationthe insoluble matter was filtered off while hot
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8f9af6b96fbd43b0bfee90504e379a47
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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