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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1892217Generated: November 2, 2026

Cesium carbonate → HCID 58476654, compound

https://huagongshe.com/reaction/1892217

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantN,N-DimethylpropargylamineHCID 81643—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
Reactant5-Bromo-2-fluoropyridin-3-amineHCID 17750144—
CatalystBis(acetonitrile)dichloropalladiumHCID 6093782—
SolventDimethylformamideHCID 6228—
ProductHCID 58476654HCID 5847665445.4%

Reaction Conditions

Temperature50 °C

Reaction Steps

A mixture of 5-bromo-2-fluoropyridin-3-amine (1.00 g, 5.24 mmol), N,N-dimethylprop-2-yn-1-amine (0.68 mL, 6.28 mmol), and cesium carbonate (3.41 g, 10.5 mmol) in DMF (25 mL) was degassed with argon for 15 min. To this slurry were added bis(acetonitrile)palladium(II) chloride (0.068 g, 0.26 mmol) and Xphos (0.324 g, 0.68 mmol). The suspension was allowed to stir at 50° C. for 4 h under an atmosphere of nitrogen and was then concentrated. The residue was purified by column chromatography to give 5-[3-(dimethylamino)prop-1-yn-1-yl]-2-fluoropyridin-3-amine (0.46 g, 45%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507667B2
Source datasetuspto-grants-2013_08
ORD IDord-7fdc022e735841c394ba4ffd1ad31d6d
Source noteuspto-grants-2013_08