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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 909293Generated: October 30, 2026

Water → HCID 58027029, compound

https://huagongshe.com/reaction/909293

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
ReactantMethyl 2-Bromo-5-nitrobenzoateHCID 245494—
Reactant(2-Methoxypyridin-3-yl)boronic acidHCID 2762709—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
ProductHCID 58027029HCID 5802702981.7%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 2-methoxypyridin-3-ylboronic acid (1.00 g, 6.54 mmol), methyl 2-bromo-5-nitrobenzoate (2.21 g, 8.50 mmol), cesium carbonate (6.39 g, 17.6 mmol) and bis(triphenylphosphine)palladium(II) dichloride (230 mg, 0.33 mmol) was suspended in anhydrous N,N-dimethylformamide (15 mL), and then the mixture was stirred under nitrogen atmosphere at 80° C. overnight. After cooling down, water (100 mL) was added thereto, and then the whole was extracted with ethyl acetate (80 mL, twice). The combined organic layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.54 g) as a yellow solid. (Yield 81%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08017775B2
Source datasetuspto-grants-2011_09
ORD IDord-42dc1fe23b2d4ad09f3486dddc0803c2
Source noteuspto-grants-2011_09