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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1475799Generated: October 31, 2026

Water → HCID 56723596, compound

https://huagongshe.com/reaction/1475799

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
ReactantMethyl 5-bromopyridine-3-carboxylateHCID 699336—
Reactant3-Chloro-4-methoxybenzeneboronic acidHCID 3247522—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
ProductHCID 56723596HCID 5672359637.3%

Reaction Steps

6.5 g of 3-chloro-4-methoxyphenylboronic acid, 5.0 g of methyl 5-bromonicotinate, 1.3 g of tetrakis(triphenylphosphine)palladium(0), and 22.6 g of Cs2CO3 were stirred in 325 ml of DMF and 65 ml of water for 3 h at 45° C. The reaction mixture was then poured into 750 ml of water and extracted three times using 300 ml of EA each. The combined organic layers were then washed twice using 150 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 2.4 g of the title compound, colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018383B2
Source datasetuspto-grants-2015_04
ORD IDord-565735d6b27c44c6a6206665729d96d3
Source noteuspto-grants-2015_04