Реакция #41620

Уравнение реакции

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

Растворители

dimethoxyethane

Условия реакции

Обработка

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

Методика

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.

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