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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 573326Generated: October 30, 2026

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

https://huagongshe.com/reaction/573326

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 58577371—
Reactant6-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-olHCID 136397690—
SolventDimethylformamideHCID 6228—
Product1-Ethyl-3-{5-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-2-yl}-1H-pyrazolo[4,3-b]pyridineHCID 6672812036.2%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (90 mg) and 6-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol (68 mg) in DMF (1 mL) was added NaH (60% in oil, 18.11 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The eluent was evaporated and the residue was crystallized from EtOH/hexane to give the title compound (38.1 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029536B2
Source datasetuspto-grants-2015_05
ORD IDord-af457ea6be4b47148d654058b1651c55
Source noteuspto-grants-2015_05