[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[N:2]2)=[CH:14][CH:13]=1A mixture of 1H-Indazole (0.50 g, 4.23 mmol), 4-methoxyphenylboronic acid (1.30 g, 8.5 mmol), triethylamine (0.86 g, 8.5 mmol) and cupric acetate ((0.77 g, 4.23 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 48 h. The reaction mixture was diluted with water and passed through a pad of Celite. The filtrate was extracted with EtOAc, washed with brine, and dried over Na2SO4. After being concentrated, the crude material was purified by a chromatography on silica gel to yield the title compound (0.32 g, 30%).
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