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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 353778Generated: October 30, 2026

Phthalimide → 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione

https://huagongshe.com/reaction/353778

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhthalimideHCID 6809—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-olHCID 23511407—
SolventTetrahydrofuranHCID 8028—
Product2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dioneHCID 2351140066%

Reaction Steps

To a solution of 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol (1 eq) in THF (20 mL) was added dropwise diethyl azodicarboxylate (1.1 eq), triphenyl phosphine (1.1 eq) and phtalimide (1.1 eq). The yellow solution was stirred at room temperature overnight and the solution was concentrated. The crude product was directly purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA to yield 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione (66%). MH+(375).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06756359B2
Source datasetuspto-grants-2004_06
ORD IDord-3d06fd0df1c24300ba3e19f032d3333a
Source noteuspto-grants-2004_06