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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 71180Generated: October 27, 2026

Dimethylformamide → 6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinonitrile

https://huagongshe.com/reaction/71180

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridineHCID 57609300—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
SolventAmmoniaHCID 222—
SolventEthyl AcetateHCID 8857—
Product6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinonitrileHCID 66608086—

Reaction Conditions

Temperature120 °C

Reaction Steps

Under a nitrogen atmosphere, to a mixture of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (25 g) and zinc cyanide (16.4 g) in DMF (250 mL) was added tetrakis(triphenylphosphine)palladium(0) (2.16 g) at room temperature, and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and 10% aqueous ammonia solution. The precipitate was collected by filtration, washed with ethyl acetate and dried to give the title compound (17.5 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822699B2
Source datasetuspto-grants-2014_09
ORD IDord-37eeb0021f474827b1f8f463763e6df1
Source noteuspto-grants-2014_09