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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 82645Generated: October 30, 2026

Sodium hydride → ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate

https://huagongshe.com/reaction/82645

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantSodium BicarbonateHCID 516892—
ReactantEthyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylateHCID 21643308—
Reactant1-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 58577603—
Solvent1,2-DimethoxyethaneHCID 8071—
Productethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylateHCID 5857756612.1%

Reaction Conditions

Temperature50 °C

Reaction Steps

The mixture of ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (504 mg), 1-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (302 mg) and NaH (67.3 mg) in DME (4 mL) was heated at 50° C. for 1 h. The mixture was heated at 200° C. for 3 h under microwave irradiation. The mixture was poured into sat. NaHCO3, and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (62.0 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846713B2
Source datasetuspto-grants-2014_09
ORD IDord-89d0ab99bb844c67b4997ec263974a67
Source noteuspto-grants-2014_09