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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2055133Generated: November 1, 2026

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

https://huagongshe.com/reaction/2055133

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 pthalimide (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 numberUS07332476B2
Source datasetuspto-grants-2008_02
ORD IDord-025219722f8b45e5b5abf267bb829062
Source noteuspto-grants-2008_02