Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 33517Generated: October 27, 2026

Cesium carbonate → 6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

https://huagongshe.com/reaction/33517

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant4-(Trifluoromethoxy)phenylboronic acidHCID 2734386—
ReactantMethyl 6-bromopyridine-2-carboxylateHCID 16217886—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
Product6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl esterHCID 6910608144.7%

Reaction Conditions

Temperature80 °C

Reaction Steps

162 mg (0.14 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 2.0 g (9.25 mmol) methyl-6-bromo-pyridine-2-carboxylate in 46 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 4.52 g (13.9 mmol) cesium carbonate and 2.1 g (10.18 mmol) of 4-(trifluoromethoxy)phenylboronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.23 g (39%) of 6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07429605B2
Source datasetuspto-grants-2008_09
ORD IDord-3228abf9434f47c796b1731712ce4c8b
Source noteuspto-grants-2008_09