Sodium Carbonate → 4-Bromo-1H-indole-2-carbonitrile

HRID 2365161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365161
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]([NH2:18])=O)[NH:11]2.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]#[N:18])[NH:11]2

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 591512734-bromo-1H-indole-2-carboxamide

Produkt 1

HCID 591513014-Bromo-1H-indole-2-carbonitrileAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Phosphorous oxychloride (1.9 mL, 20 mmol) was added to a suspension of 4-bromo-1H-indole-2-carboxylic acid amide (1.32 g, 5.5 mmol.) in toluene (10 mL) and the mixture was stirred at reflux for 45 min. On cooling, the mixture was poured into an aqueous Na2CO3 solution (sat., 50 mL) and the mixture stirred until effervescence had subsided. The layers were separated, the aqueous phase extracted with EtOAc and the combined organic layers dried (MgSO4) and evaporated to dryness. The crude material was purified by column chromatography to afford the title compound as a solid (1.00 g, 82%).

Aufarbeitung

  1. temperatureat reflux for 45 min
  2. temperatureOn cooling
  3. stirringthe mixture stirred until effervescence
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with EtOAc
  6. dry with materialthe combined organic layers dried (MgSO4)
  7. customevaporated to dryness
  8. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6ddc06bd0bf048cbac98276d23aa3f70
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697693B2

Notizen zur Reaktion

Wird geladen…