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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2406689Generated: November 2, 2026

Cesium carbonate → HCID 86683845, compound

https://huagongshe.com/reaction/2406689

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1,4-DioxaneHCID 31275—
Reactant3,5-DibromopyridineHCID 69369—
Reactant1-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 2734321—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
ProductHCID 86683845HCID 8668384553.5%

Reaction Steps

Cesium carbonate (165 mg), 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (136 mg) and Pd(PPh3)4 (24 mg) were added to a 1,4-dioxane (4 ml) solution containing 3,5-dibromopyridine (100 mg), followed by reflux for 4 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=4:1), and a white solid of tert-butyl2-(5-bromopyridin-3-yl)-1H-pyrrol-1-carboxylate (73 mg) was thus obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08809371B2
Source datasetuspto-grants-2014_08
ORD IDord-34a2be97d2704375ad5248ad3a2bb08f
Source noteuspto-grants-2014_08