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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1072917Generated: November 3, 2026

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

https://huagongshe.com/reaction/1072917

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantDimethylformamideHCID 6228—
Reactant1,3-Bis(diphenylphosphino)propaneHCID 81219—
Reactant5-bromo-2-methyl-3H-imidazo[4,5-b]pyridineHCID 22387961—
Catalystpalladium(II) acetateHCID 167845—
SolventTriethylamineHCID 8471—
ProductMethyl 2-methyl-3h-imidazo[4,5-b]pyridine-5-carboxylateHCID 22387777—

Reaction Conditions

Temperature85 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06911469B2
Source datasetuspto-grants-2005_06
ORD IDord-cda1b0a2bd7c431eb35bf83745d2db7a
Source noteuspto-grants-2005_06