Reaktion #41620

Reaktionsgleichung

1-(t-butoxycarbonyl)pyrrole-2-boronic acid

sodium carbonate

water

4-bromo-5-(4-methanesulfonyl-phenoxy)-2-nitro-phenylamine

→

t-butyl 2-(4-amino-2-(4-methanesulfonyl-phenoxy)-5-nitro-phenyl)-pyrrole-1-carboxylate

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction liquid
2. 2
   TemperaturAfter cooled
3. 3
   Sonstigethe reaction liquid
4. 4
   Filtrationwas filtered through Celite
5. 5
   workup.ADDITIONthe filtrate was diluted with ethyl acetate
6. 6
   Waschenwashed with water and saturated saline in order
7. 7
   Trocknendried with anhydrous magnesium sulfate
8. 8
   SonstigeThe solvent was evaporated away under reduced pressure
9. 9
   Sonstigethe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
10. 10
    Sonstigeto obtain the entitled compound as a brown oily substance

Vorschrift

7.9 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid, 1.8 g of dichlorobistriphenylphosphine palladium, 50 ml of aqueous saturated sodium carbonate solution and 50 ml of water were added in order to a dimethoxyethane (100 ml) solution of 10.3 g of 4-bromo-5-(4-methanesulfonyl-phenoxy)-2-nitro-phenylamine, and the reaction liquid was stirred in a nitrogen atmosphere at 80° C. for 1 hour. After cooled, the reaction liquid was filtered through Celite, the filtrate was diluted with ethyl acetate, washed with water and saturated saline in order, and then dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound as a brown oily substance.

Quelle