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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1642792Generated: November 3, 2026

Sodium Carbonate → HCID 58002512, compound

https://huagongshe.com/reaction/1642792

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantEthyl 5-bromopyridine-3-carboxylateHCID 140785—
Reactant4-(Trifluoromethyl)phenylboronic acidHCID 2734389—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 58002512HCID 58002512—

Reaction Conditions

Temperature85 °C

Reaction Steps

6.74 g (29.3 mmol) of ethyl 5-bromonicotinate, 8.35 g (43.9 mmol) of 4-trifluoromethylphenylboronic acid, 0.17 g (0.15 mmol) of tetrakis(triphenylphosphine)palladium(0) and 6.21 g (58.6 mmol) of sodium carbonate were dissolved in a mixture of 75 ml of 1,2-dimethoxyethane, 15 ml of water and 184 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 100:2→100:5). Yield: 6.22 g (72% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119663B2
Source datasetuspto-grants-2012_02
ORD IDord-2ac859037919432a8e3ea694a9307288
Source noteuspto-grants-2012_02