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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 505109Generated: November 1, 2026

Sodium Carbonate → HCID 66743454, compound

https://huagongshe.com/reaction/505109

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant4-BromopyridineHCID 14268—
ReactantAmmonium ChlorideHCID 25517—
Reactant5-Bromo-2,3-dihydrobenzo[b]furan-7-boronic AcidHCID 2794805—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventDimethoxyethane ethanolHCID 20074477—
ProductHCID 66743454HCID 6674345476%

Reaction Conditions

Temperature50 °C

Reaction Steps

4-Bromopyridine or hydrochloride salt thereof was dissolved in DME under argon and Pd(Ph3P)4 (3 mol %) was added. The mixture was stirred for 10 min at 50° C. To this solution was added (commercially available) 5-bromo-2,3-dihydrobenzo[b]furan-7-boronic acid dissolved in a minimum amount of EtOH/DME 1:2 followed by 2N Na2CO3. The reaction mixture was refluxed (110° C.) under stirring for 2 h. The flask was cooled to RT, the mixture was treated with sat. aq. NH4Cl solution and extracted with CHCl3. Evaporation and purification by SiO2 gel chromatography (hexane/ethyl acetate: 4/1) gave the title compound in 76% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07781436B2
Source datasetuspto-grants-2010_08
ORD IDord-bf719ac7a442458b8c40406b78230662
Source noteuspto-grants-2010_08