COCCN1CCN(C2C=CC(C=O)=C([N+]([O-])=O)C=2)CC1.[Br-].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1
A solution of 4-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde (0.23 g, 0.68 mmol) obtained in Step 1 was dissolved in methanol (8.0 mL) and the solution was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.32 g, 0.68 mmol) and potassium carbonate (0.19 g, 1.4 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain (E)-3-{2-[4-(2-methoxyethyl)piperazin-1-yl]-2-nitrophenyl}vinyl}-1H-indazole (0.48 g, 100%).
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