Methanol → Methyl 2-methyl-3h-imidazo[4,5-b]pyridine-5-carboxylate
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].[CH3:46][OH:47]>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:46]([O:44][CH3:43])=[O:47])=[CH:32][CH:33]=2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
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 placed in an autoclave, and N,N-dimethylformamide (18.6 ml), methanol (14.9 ml) and triethylamine (5.4 ml) were added thereto. The mixture was stirred at 85° C. for 14 hr at 10 atm under a carbon monoxide atmosphere. The reaction mixture was cooled and the solvent was evaporated. To the residue was added methanol (60 ml), and the mixture was heated. The insoluble matter was filtered off while the mixture was hot. The filtrate was concentrated to give the objective compound (2.95 g) as a white powder.
Workup
- additionwere added
- temperatureThe reaction mixture was cooled
- customthe solvent was evaporated
- additionTo the residue was added methanol (60 ml)
- temperaturethe mixture was heated
- filtrationThe insoluble matter was filtered off while the mixture
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-cda1b0a2bd7c431eb35bf83745d2db7a
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911469B2
Reaction notes
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