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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 82599Generated: October 29, 2026

Sodium hydride → 1-(difluoromethyl)-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

https://huagongshe.com/reaction/82599

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant2-chloro-1-methyl-1H-1,3-benzodiazoleHCID 663080—
Reactant1-(difluoromethyl)-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 58577672—
SolventMethanolHCID 887—
SolventDimethylformamideHCID 6228—
Product1-(difluoromethyl)-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 5857768846.7%

Reaction Conditions

Temperature180 °C

Reaction Steps

2-Chloro-1-methyl-1H-benzimidazole (70 mg) was added to a solution of 1-(difluoromethyl)-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (122 mg) and NaH (25.2 mg) in DMF (3 mL) at 100° C. The mixture was heated at 180° C. for 1 h under microwave irradiation. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 1-(difluoromethyl)-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (80 mg) as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846713B2
Source datasetuspto-grants-2014_09
ORD IDord-4fda86ac8f1e40d1805d996b849fb6b7
Source noteuspto-grants-2014_09