Dimethylformamide → 6-fluoro-1H-indole-7-carbonitrile

HRID 1512838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512838
Br[C:2]1[C:3]([F:11])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[F:11][C:3]1[C:2]([C:12]#[N:13])=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 269860207-Bromo-6-fluoro-1H-indole

Produkt 1

HCID 591461546-fluoro-1H-indole-7-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Versuchsvorschrift

To a solution of 7-bromo-6-fluoro-1H-indole (D140) (1.0 g) in DMF (15 ml) were added Zn(CN)2 (2.2 g) and then Pd(PPh3)4 (1.1 g) in a microwave tube, then N2 atmosphere was bubbled in. The sealed vial was irradiated in the microwave at 150° C. for 2 hours. After cooling, DCM (80 mL) was added to the resulting mixture which was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to afford 6-fluoro-1H-indole-7-carbonitrile (D141) (0.5 g) as a white solid.

Aufarbeitung

  1. customPd(PPh3)4 (1.1 g) in a microwave tube, then N2 atmosphere was bubbled in
  2. customThe sealed vial was irradiated in the microwave at 150° C. for 2 hours
  3. temperatureAfter cooling
  4. additionDCM (80 mL) was added to the resulting mixture which
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-247d7a7e8a1941ce8b8595bbc887034c
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217028B2

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