[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[C:5]([O:12][CH3:13])[CH:4]=1)=[CH2:2].[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:17]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([F:14])[CH:16]=2)=[C:5]([O:12][CH3:13])[CH:4]=1)=[CH2:2]To a solution of 6-ethenyl-4-(methyloxy)-1H-indole (D8) (665 mg, 3.84 mmol) in dichloromethane (20 mL) was added 3-fluoro-4-methoxyphenylboronic acid (1.31 g, 7.71 mmol), triethylamine (1.1 mL, 7.91 mmol), copper (II) acetate (1.39 g, 7.68 mmol) and powdered 4A molecular sieves (1.0 g). The reaction mixture was stirred at room temperature in the presence of air for 18 hours. Further quantities of 3-fluoro-4-methoxyphenylboronic acid (330 mg), triethylamine (0.28 mL) and copper acetate (340 mg) were added and the mixture stirred at room temperature in the presence of air for a further 48 hours. The mixture was filtered and the solid washed with dichloromethane. The filtrate was concentrated at reduced pressure. The product was purified by silica gel chromatography eluting with 5-50% dichloromethane in hexane to yield the title compound (D9), (541 mg).
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