Acetic Acid → 4-(2,6-Difluoro-phenyl)-1,3-dihydro-indol-2-one

HRID 1839624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839624
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[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:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[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 225617024-(2,6-difluoro-phenyl)-1H-indole

Produkt 1

HCID 225617464-(2,6-Difluoro-phenyl)-1,3-dihydro-indol-2-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To the suspension of 4-(2,6-difluoro-phenyl)-1H-indole (9.5 g, 41.4 mmol) in t-BuOH:ethanol:acetic acid (262 mL:155 mL:81 mL) was added pyridinium tribromide (40.28 g, 126 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added more acetic acid (200 mL). Zinc dust (14.2 g, 217 mmol) was added to the reaction mixture portionwise. After stirring for one hour, the 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×), sat. NaHCO3 (2×), brine (3×), dried over Na2SO4, concentrated, triturated with ether to give 7.1 g (70%) of 4-(2,6-difluoro-phenyl)-1,3-dihydro-indol-2-one as a white solid.

Aufarbeitung

  1. stirringAfter stirring for one hour
  2. filtrationthe 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×), sat. NaHCO3 (2×), brine (3×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-84f0a34efadd442c90f6b1ec4a29bbb1
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677368B2

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