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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 572183Generated: November 1, 2026

Dimethylformamide → 3-Ethyl-1-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[3,4-b]pyridine

https://huagongshe.com/reaction/572183

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium hydrideHCID 24758—
Reactant3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 58577371—
Reactant4-(3-Ethyl-1H-pyrazolo[3,4-b]pyridin-1-yl)phenolHCID 86704983—
SolventMethanolHCID 887—
Product3-Ethyl-1-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[3,4-b]pyridineHCID 8670499064.6%

Reaction Conditions

Temperature180 °C

Reaction Steps

To a mixture of 4-(3-ethyl-1H-pyrazolo[3,4-b]pyridin-1-yl)phenol (120 mg) obtained in Example 8, step D), sodium hydride (60% in oil, 20.1 mg) and DMF (5.0 ml) was added 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (106 mg), and the mixture was stirred under microwave irradiation at 180° C. for 1 hr. The reaction mixture diluted with methanol, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (120 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029388B2
Source datasetuspto-grants-2015_05
ORD IDord-e2b409e99f304e3a821c15e02aea694b
Source noteuspto-grants-2015_05