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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1642797Generated: November 2, 2026

Sodium Carbonate → HCID 58002238, compound

https://huagongshe.com/reaction/1642797

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantEthyl 5-bromopyridine-3-carboxylateHCID 140785—
Reactant4-(Trifluoromethoxy)phenylboronic acidHCID 2734386—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 58002238HCID 58002238—

Reaction Conditions

Temperature85 °C

Reaction Steps

3.35 g (14.6 mmol) of ethyl 5-bromonicotinate, 4.50 g (21.9 mmol) of 4-(trifluoromethoxy)-phenylboronic acid, 0.84 g (0.73 mmol) of tetrakis(triphenylphosphine)palladium(0) and 3.01 g (29.1 mmol) of sodium carbonate were dissolved in a mixture of 38 ml of 1,2-dimethoxyethane, 7.5 ml of water and 91 ml of dimethylformamide and stirred at 85° C. for 18 h. For work-up, some of the dimethylformamide was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over sodium sulphate and the crude product was purified by flash chromatography (dichloromethane/acetonitrile 100:0→100:5). Yield: 2.64 g (55% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119663B2
Source datasetuspto-grants-2012_02
ORD IDord-6595a1ae45ec4aca95e5723e9c2fe6bf
Source noteuspto-grants-2012_02