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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 927429Generated: October 25, 2026

Cesium carbonate → 6-(3-Chloro-phenyl)-5-cyclopropyl-pyridine-2-carboxylic acid methyl ester

https://huagongshe.com/reaction/927429

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant(3-Chlorophenyl)boronic acidHCID 2734323—
Reactant6-Bromo-5-cyclopropyl-pyridine-2-carboxylic acid methyl esterHCID 86674750—
CatalystHCID 178418807HCID 178418807—
Solvent1,4-DioxaneHCID 31275—
Product6-(3-Chloro-phenyl)-5-cyclopropyl-pyridine-2-carboxylic acid methyl esterHCID 7108793671%

Reaction Conditions

Temperature110 °C

Reaction Steps

6-Bromo-5-cyclopropyl-pyridine-2-carboxylic acid methyl ester (0.1 g, 0.4 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.08 g, 0.5 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium(II)dichloride methylene chloride adduct (CAN 95464-05-4, 50 mg) and cesium carbonate (CAN 534-17-8, 0.2 g, 0.6 mmol) was added into 1,4-dioxane (10 mL) under nitrogen atmosphere. The mixture was stirred for 12 h at 110° C. Subsequently, the mixture was concentrated to give crude product. The crude product was purified by a flash column chromatography (silica gel, 5 g, 20% ethyl acetate in petroleum ether) to give product (80 mg, 71%); MS: (EI) m/e 288.1 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290451B2
Source datasetuspto-grants-2016_03
ORD IDord-cb92640b67e443148af5591fe61562bd
Source noteuspto-grants-2016_03