Reaktion #41439

Reaktionsgleichung

KOtBu

2-fluoro-5-iodobenzaldehyde

cyclopentylhydrazine

cesium carbonate

→

1-Cyclopentyl-5-iodo-1H-indazole

Lösungsmittel

DMF

ethyl acetate

acetonitrile

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 150° C. for 5 h
2. 2
   TemperaturAfter cooling to r.t.
3. 3
   Waschenwashed with water (3×50 ml)
4. 4
   Sonstigedried
5. 5
   SonstigeEvaporation of solvent
6. 6
   Sonstigeafforded batch residue, which
7. 7
   Sonstigethe insoluble material was removed by filtration
8. 8
   SonstigeFlash chromatography on silica gel (n-heptane/ethyl acetate) afforded yellow oil, 158 mg (25%)

Vorschrift

A mixture of 2-fluoro-5-iodobenzaldehyde (500 mg, 2 mmol), cyclopentylhydrazine (273 mg, 2 mmol), and cesium carbonate (1.91 g, 5 mmol) in NMP (5 ml) was stirred at 100° C. overnight. Then KOtBu (560 mg, 5 mmol) and DMF (10 ml) were added, and the mixture was stirred at 150° C. for 5 h. After cooling to r.t., the mixture was diluted with ethyl acetate (100 ml), and washed with water (3×50 ml), and dried. Evaporation of solvent afforded batch residue, which was dissolved in acetonitrile (50 ml), and the insoluble material was removed by filtration. Flash chromatography on silica gel (n-heptane/ethyl acetate) afforded yellow oil, 158 mg (25%).

Quelle