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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2246450Generated: November 1, 2026

Chloroacetaldehyde → 2-(3-Chloro-propenyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

https://huagongshe.com/reaction/2246450

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroacetaldehydeHCID 33—
ReactantEthanolHCID 702—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant[4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chlorideHCID 86613868—
SolventTetrahydrofuranHCID 8028—
Product2-(3-Chloro-propenyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrileHCID 68517725—

Reaction Steps

A solution of [4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chloride (167.2 mg, 0.26 mmol), chloroacetaldehyde (50% in water) (32,6 mg, 0.41 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (62.4 mg, 0.41 mmol) was dissolved in a 1:1 mixture of THF:ethanol (4 ml) at room temperature overnight. The mixture was concentrated and purified on preparative HPLC to afford the title compound. MS m/z 407.5 (m+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07687515B2
Source datasetuspto-grants-2010_03
ORD IDord-094a89ad82b9434b91a59d1263b1b3c2
Source noteuspto-grants-2010_03