Ammonium Hydroxide → 1H-pyrrolo(2,3-b)pyridin-5-amine

HRID 40860

Reaktionsgleichung

Reaktionsgleichung von HRID 40860
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[NH4+:12]>CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH:8]1[C:5]2=[N:6][CH:7]=[C:2]([NH2:12])[CH:3]=[C:4]2[CH:10]=[CH:9]1

Komponenten

5

Edukt 2

HCID 14923Ammonium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-bromo-1H-pyrrolo[2,3-b]pyridine (6.0 g, 30.45 mmol) in ammonium hydroxide (120 mL) was treated with copper sulphate pentahydrate (1.50 g, 6.09 mmol, 0.2 eq) and heated in a sealed tube overnight. The reaction was diluted with EtOAc and the insoluble black solid was filtered off. The filtrate was extracted (EtOAc/Water) and the organic layer washed with saturated aqueous ammonium chloride, followed by water and brine. The organics were dried over magnesium sulphate, filtered and evaporated to dryness to give the product as a pale brown solid (2.57 g, 63%)

Aufarbeitung

  1. temperatureheated in a sealed tube overnight
  2. filtrationthe insoluble black solid was filtered off
  3. extractionThe filtrate was extracted (EtOAc/Water)
  4. washthe organic layer washed with saturated aqueous ammonium chloride
  5. dry with materialThe organics were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3922a1d6c350499993d460cc3cc0efb4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530489B2

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