[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][CH:2]=1To a stirred solution of 1H-indole-5-carbaldehyde (0.50 g, 3.44 mmol) in DCM (25 mL) was added N-chlorosuccinimide (0.44 g, 3.27 mmol). After 4 h, the mixture was washed with water (50 mL) and the organic layer was dried and concentrated to obtain the crude residue (0.62 g), which was used without purification. 1H NMR (CDCl3): 10.04 (s, 1H), 8.17-8.15 (m, 1H), 7.79 (dd, J=8.6, 1.5 Hz, 1H), 7.46 (d, J=8.6 Hz, 1), 7.29-7.28 (m,1H).
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