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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 238370Generated: October 25, 2026

Ethanol → 2-Methyl-1'H,2H-3,4'-bipyrazole

https://huagongshe.com/reaction/238370

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantSodium CarbonateHCID 10340—
Reactant5-Iodo-1-methyl-1H-pyrazoleHCID 13334065—
Reactant1-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acidHCID 44118675—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product2-Methyl-1'H,2H-3,4'-bipyrazoleHCID 13638777632.9%

Reaction Conditions

Temperature100 °C

Reaction Steps

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (750 mg), [1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid (1.27 g), tetrakis(triphenylphosphine)palladium(0) (209 mg), 2 M sodium carbonate aqueous solution (3.6 mL), ethanol (3.6 mL) and toluene (7.2 mL) was stirred at 100° C. for 14 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10), so as to obtain the title compound (176 mg) in the form of a light yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08642626B2
Source datasetuspto-grants-2014_02
ORD IDord-a540602f3ca5468981ff4c7803c95013
Source noteuspto-grants-2014_02