Reaction #41620

Reaction equation

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

Solvents

dimethoxyethane

Conditions

Workup

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

Procedure

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