Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>COCCOC>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]([CH:12]=[O:13])=[CH:10]2A mixture of 2,8-dichloroquinoline-3-carbaldehyde (2.0 g, 8.85 mmol), 2M aqueous Na2CO3 solution (8 mL), phenylboronic acid (1.5 g, 12.3 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.25 g, 0.216 mmol) in DME (30 mL) was degassed and the mixture heated at 110° C. for 4 h. The mixture was allowed to cool to room temperature, diluted with EtOAc and washed with brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The resultant solid was triturated in ether, filtered, washed with small amount of ether, then light petroleum, and dried, to give the title compound (2.3 g, 97%) as an off-white solid. δH (CDCl3) 10.25 (s, 1H), 8.86 (s, 1H), 7.95-8.02 (m, 2H), 7.78-7.14 (m, 2H), 7.54-7.62 (m, 4H). LCMS (ES+) 268 (M+H)+, RT 1.98 minutes.
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