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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2279138Generated: October 30, 2026

Water → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

https://huagongshe.com/reaction/2279138

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium CarbonateHCID 11430—
Reactant4-(Methoxymethoxy)phenylboronic acidHCID 2762528—
Reactant6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl esterHCID 86680319—
SolventEthyl AcetateHCID 8857—
SolventWater 1,2-dimethoxyethaneHCID 18180031—
Product6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl esterHCID 90013795107.1%

Reaction Conditions

Temperature85 °C

Reaction Steps

To a degassed mixture of 1.68 g 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester, 1.00 g 4-(methoxymethoxy)-phenylboronic acid and 0.70 g potassium carbonate in DME/water (v/v=2/1, 24 mL) at r.t. and under Ar-atmosphere 70 mg palladium(0) bis(tri-tert-butylphosphine) was added and the mixture was stirred at 85° C. for 1 h. To the mixture water and ethyl acetate were added, the phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. 2.08 g (100%) of the title compound were obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09133181B2
Source datasetuspto-grants-2015_09
ORD IDord-5604f7e767dd46a0910abfac81f3d725
Source noteuspto-grants-2015_09