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

HRID 1296170

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH2:27]([N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[CH:28]=[CH2:29].C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:40]=[C:31]1[C:32]2[C:33](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](=[O:35])[N:30]1[CH2:27]/[CH:28]=[CH:29]/[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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 K2CO310%. 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.).

Aufarbeitung

washwashed with K2CO310%
customThe organic layer was separated
customdried
filtrationfiltered
customthe solvent was evaporated
customThe residue was crystallized from ACN
filtrationThe precipitate was filtered off
customdried

Quellen und Nachweise

ORD-Eintrag: ord-7a8148ccc085463590a83d1d023e0bfd
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07244848B2

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