CS(O[CH2:6]/[CH:7]=[CH:8]\[CH2:9]OS(C)(=O)=O)(=O)=O.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:15][C:16]1[CH:17]=[C:18]([N:19]2[CH2:9][CH:8]=[CH:7][CH2:6]2)[CH:20]=[CH:21][CH:22]=1Then, a mixture of 15 g of the cis-1,4-bis(methanesulfonyloxy)-2-butene, 10 g of 3-bromoaniline, 24 g of anhydrous potassium carbonate and 70 ml of N,N-dimethylformamide was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography with 5% ethyl acetate/hexane, to give 6.6 g of the title compound.
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