Réaction #41620

Équation de réaction

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

Solvants

dimethoxyethane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source