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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 494157Generated: October 25, 2026

Triethylamine → N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

https://huagongshe.com/reaction/494157

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantN-AllylphthalimideHCID 224401—
ReactantN-(4-iodophenyl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideHCID 21895284—
Catalystpalladium(II) acetateHCID 167845—
SolventDichloromethaneHCID 6344—
ProductN-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideHCID 2189528850.6%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of intermediate (1) (0.012 mol), N-allyl-phthalimide (0.012 mol), palladium(II) acetate (0.001 mol) and triethylamine (0.024 mol) was stirred at 100° C. for 12 hours in a bomber, then dissolved in DCM and washed with K2CO3 10%. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 3.2 g of N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 2; mp. 190° C.).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07538124B2
Source datasetuspto-grants-2009_05
ORD IDord-74177f64702f4b5ea71e9855ace6de15
Source noteuspto-grants-2009_05