Reacción #41620

Ecuación de reacción

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

Disolventes

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente