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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1890742Generated: October 31, 2026

Toluene → 2-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dione

https://huagongshe.com/reaction/1890742

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
Reactant2-(Tributylstannyl)pyridineHCID 607784—
Reactant2-(6-Bromo-5-methylpyridin-2-yl)isoindoline-1,3-dioneHCID 58317950—
CatalystHCID 178418397HCID 178418397—
SolventEthyl AcetateHCID 8857—
Product2-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dioneHCID 58317915—

Reaction Conditions

Temperature116 °C

Reaction Steps

To a reaction vessel under argon containing 2-(6-bromo-5-methylpyridin-2-yl)isoindoline-1,3-dione (85 mg, 0.27 mmol), 2-(tributylstannyl)pyridine (123 mg, 0.32 mmol), Pd(PPh3)4(31 mg, 0.027 mmol) is added anhydrous toluene (0.7 ml). The mixture is heated to 116° C. with an oil bath for 18 hours, cooled to room temperature, diluted with ethyl acetate and filtered through a celite pad to remove any solids. The filtrate is concentrated to afford 2-(3-methyl-2,2′-bipyridin-6-yl)isoindoline-1,3-dione as a brown solid (LC-MS m/z: 316.1 (M+1)) which is used without further purification in the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507491B2
Source datasetuspto-grants-2013_08
ORD IDord-ec59e03480a847b6aa8065580ac7160c
Source noteuspto-grants-2013_08