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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 573355Generated: October 30, 2026

Water → 6-Fluoro-1-(1-methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine

https://huagongshe.com/reaction/573355

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 58577371—
Reactant4-[6-Fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenolHCID 136409092—
SolventDimethylformamideHCID 6228—
Product6-Fluoro-1-(1-methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridineHCID 8668899453.2%

Reaction Steps

To a stirred solution of 4-[6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenol (76 mg) in DMF (4 mL) was added NaH (60% in oil, 11.2 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (59.2 mg) was added. The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The product was crystallized from AcOEt/hexane to give the title compound (60.0 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029536B2
Source datasetuspto-grants-2015_05
ORD IDord-d47baa43603342b996cc329c0455c85f
Source noteuspto-grants-2015_05