Acetic Acid → HCID 22561714, Verbindung

HRID 983033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 983033
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2.C([OH:20])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:20])[NH:13]2

Komponenten

7

Edukt 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561815HCID 22561815, Verbindung

Produkt 1

HCID 22561714HCID 22561714, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To the suspension of 4-(2,4-difluoro-phenyl)-1H-indole (6.42 g, 28 mmol) in t-BuOH: ethanol: acetic acid (177 mL: 105 mL: 55 mL) was added pyridinium tribromide (27 g, 84 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added with acetic acid (136 mL). Zinc dust (9.8 g, 150 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (5×), neutralized with 1N HCl, washed with sat. NaHCO3, brine, dried over Na2SO4, concentrated and triturated with ether to give 5.16 g (75%) of 4-(2,4-difluoro-phenyl) 1,3-dihydro-indol-2-one.

Aufarbeitung

  1. stirringAfter stirring for one hour
  2. filtrationany unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (5×)
  6. washwashed with sat. NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customtriturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-d95acc4deb5648e7b030f382ed5fc331
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861418B2

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