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 494157

Reaktionsgleichung

Reaktionsgleichung von HRID 494157
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

6

Edukt 3

HCID 8471TriethylamineHCID 224401N-AllylphthalimideHCID 21895284N-(4-iodophenyl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

Produkt 1

HCID 21895288N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

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 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.).

Aufarbeitung

  1. washwashed with K2CO3 10%
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from ACN
  7. filtrationThe precipitate was filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-74177f64702f4b5ea71e9855ace6de15
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538124B2

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