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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1929821Generated: October 29, 2026

Citric Acid → HCID 86619566, compound

https://huagongshe.com/reaction/1929821

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
ReactantSodium CarbonateHCID 10340—
Reactant2-Amino-3,5-dibromopyrazineHCID 620004—
Reactant2-Chlorophenylboronic acidHCID 2734322—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 86619566HCID 8661956654%

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0.24 g) is added at room temperature to a solution of 2-amino-3,5-dibromopyrazine (0.51 g) in dimethoxyethane (12 mL). The mixture is stirred for 30 min and sodium carbonate (0.53 g), water (6 mL) and 2-chlorophenylboronic acid (0.32 g) are added and the mixture is stirred for 18 h at 100° C. The mixture is cooled, citric acid (10%, 20 mL) is added and the mixture is extracted with ethyl acetate (3×50 mL). Organic phases were pooled, washed with sodium bicarbonate and brine, dried with Na2SO4 and the solvent was evaporated. The residue was purified by chromatography on silica gel with dichloromethane to yield 0.31 g of the title compound as a white solid, mp 138.5-139.5° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08188093B2
Source datasetuspto-grants-2012_05
ORD IDord-93f4dd944ffe48d8a0b894fbe5847d0e
Source noteuspto-grants-2012_05