[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=1[Br:24].[CH3:25][CH2:26]N=C=NCCCN(C)C.Cl.O>CN(C=O)C>[Br:24][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([O:23][CH2:25][CH3:26])=[O:22])[CH:18]=[CH:19][C:14]=1[NH:13][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12]
In DMF (20 ml) were dissolved indole-3-carboxylic acid (1.00 g, 6.21 mmol) and 4-amino-3-bromophenylacetic acid (1.60 g, 6.21 mmol). To the resulting solution was added EDC HCl (1.43 g, 7.45 mmol) under stirring at room temperature. After the reaction mixture was stirred at room temperature for 4 hours, water was added thereto, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, ethyl (3-bromo-4-((3-indolylcarbonyl)amino)phenyl)acetate (664 mg, 27%) was obtained as a pale yellow solid.
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