Ammonia → 4-Fluoro-1H-indole-7-carbonitrile

HRID 992351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992351
[F:1][C:2]1[CH:10]=[CH:9][C:8](Br)=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:12]([Cu])#[N:13].N>CN(C=O)C.CO>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:12]#[N:13])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 43429567-bromo-4-fluoro-1H-indoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 224730224-Fluoro-1H-indole-7-carbonitrileAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-fluoro-7-bromoindole (600 mg, 2.8 mmol) and CuCN (1.004 g, 11.2 mmol) in DMF (4 ml) was refluxed for 16 hours. After cooling to room temperature, the reaction mixture was poured into a solution of ammonia in MeOH (30 ml, sat.) and the residue removed by filtration. The filtrate was added to a mixture of water (20 ml)/ammonia (20 ml, sat. aq.) and extracted with EtOAc/Ether (1/1) until TLC analysis showed no product in the aqueous phase. The combined organic extracts were washed with brine (2×200 ml) and water (200 ml), dried (MgSO4); evaporation in zacuo gave 4-fluoro-7-cyanoindole as a tan yellow solid (310 mg, 69%).

Aufarbeitung

  1. temperaturewas refluxed for 16 hours
  2. customthe residue removed by filtration
  3. additionThe filtrate was added to a mixture of water (20 ml)/ammonia (20 ml, sat. aq.)
  4. extractionextracted with EtOAc/Ether (1/1) until TLC analysis
  5. washThe combined organic extracts were washed with brine (2×200 ml) and water (200 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporation in zacuo

Quellen und Nachweise

ORD-Eintrag
ord-2a98c6b8d0bb41b5a996257b6867f73e
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469006B1

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