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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1778740Generated: October 25, 2026

Dichloromethane → (6-ethyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)boronic acid

https://huagongshe.com/reaction/1778740

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantPotassium AcetateHCID 517044—
ReactantBis(pinacolato)diboraneHCID 2733548—
Reactant3-bromo-6-ethyl-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-oneHCID 86722840—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
Solvent1,4-DioxaneHCID 31275—
Product(6-ethyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)boronic acidHCID 8672284153.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 3-bromo-6-ethyl-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one (240 mg, 1.0 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (250 mg, 1.0 mmol), potassium acetate (290 mg, 3.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complexed with dichloromethane (1:1) (30 mg, 0.04 mmol) in 1,4-dioxane (10 mL) was degassed and stirred at 100° C. for 6 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.11 g). LCMS (M+H)+=207.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09266892B2
Source datasetuspto-grants-2016_02
ORD IDord-bf5f12b79fa34619b3b0fc51bd4d8aac
Source noteuspto-grants-2016_02