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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1909185Generated: October 31, 2026

Ethyl Acetate → HCID 68295298, compound

https://huagongshe.com/reaction/1909185

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium CarbonateHCID 10340—
Reactant[3-(Hydroxymethyl)phenyl]boronic acidHCID 2734662—
Reactant6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamideHCID 86703409—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 68295298HCID 6829529880.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

A solution of 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (2.5 g, 5.98 mmol), (3-(hydroxymethyl)phenyl)boronic acid (1 g, 6.57 mmol) and Pd(PPh3)4 (0.69 g, 0.598 mmol) in 1,4-dioxane (30 mL) was purged with argon for 10 min. Then, 2 M Na2CO3 (2.3 g, 21.69 mmol) in water was added to it and again argon was purged through it for 10 min. The reaction mixture was stirred at 100° C. for 2 h. After completion of the reaction, water was added to it and extraction was carried out using EtOAc. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give the desired compound (2.1 g, 80.7%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598167B1
Source datasetuspto-grants-2013_12
ORD IDord-1b946519c5c34307a01797447c7fd96d
Source noteuspto-grants-2013_12