Reaktion #44268

ord-c0952ee84e994226b7dcb2797003c9a7

Reaktionsgleichung

Brc1cnc2nnn(Cc3ccc4ncccc4c3)c2n1
6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline
Cc1c[nH]cn1
4-methyl-1H-imidazole
[Cs+].[F-]
CsF
Cc1cn(-c2cnc3nnn(Cc4ccc5ncccc5c4)c3n2)cn1
6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline
Ausbeute 56.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
160°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe resulting suspension was filtered
  2. 2
    WaschenThe precipitate was washed with water
  3. 3
    Sonstigepurified by column chromatography
  4. 4
    Waschenelution with methanol and dichloromethane

Vorschrift

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (50 mg, 0.15 mmol), 4-methyl-1H-imidazole (36 mg, 0.44 mmol) and CsF (25 mg, 0.16 mmol) in acetonitrile (1.45 mL) was heated in a microwave to 160° C. for 20 minutes. The reaction was diluted with water (5 mL) and the resulting suspension was filtered. The precipitate was washed with water and then purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (28 mg, yield 56%)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732604B2uspto-grants-2010_06