[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=[O:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2.[Br:13]Br>C(O)(=O)C.C(Cl)Cl>[Br:13][C:5]1[C:4]2[C:8](=[C:9]([CH:11]=[O:12])[CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][N:6]=1To a mixture of 5-chloro-1H-indazole-7-carbaldehyde (1.0 g, 5.54 mmol) in acetic acid (5 mL) was added bromine (0.43 mL, 8.31 mmol) slowly over 5 min. After 1 h, the reaction mixture was diluted with methylene chloride, washed with water (2×), saturated sodium thiosulfate (2×), saturated sodium bicarbonate (2×), then brine (2×), dried over sodium sulfate, and concentrated to afford 1.4 g (97%) as a yellow powder. LC/MS (HPLC method 1): tR=2.49 min, 261.00(MH)+.
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