반응 #56675

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5-Chloro-2-(piperazin-1-ylsulphonyl)-1H-indole

4-carboxyphenyl boronic acid

O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

→

4-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid

수율 56.0%

용매

N,N-dimethylformamide

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후처리

1. 1
   기타N,N-Dimethylformamide was removed in vacuo
2. 2
   기타the crude was purified by flash chromatography three times (dichloromethane/methanol, 100-98/2)

실험 절차

5-Chloro-2-(piperazin-1-ylsulphonyl)-1H-indole (5.42 g, 18.1 mmol) was added to a solution of 4-carboxyphenyl boronic acid (3.00 g, 18.1 mmol) N,N-diisopropylethylamine (2.34 g, 18.1 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (5.81 g, 18.1 mmol) in 80 mL N,N-dimethylformamide, the mixture was stirred for 2 hours at room temperature. N,N-Dimethylformamide was removed in vacuo and the crude was purified by flash chromatography three times (dichloromethane/methanol, 100-98/2) to give 4-({4-[(5-chloro-1H-indol-2-yl)sulphonyl]piperazin-1-yl}carbonyl)phenyl boronic acid as a colourless solid (56% yield).

출처