FC(F)(F)S(O[C:7]1[C:8]([Br:19])=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[N:13]=[C:12]([CH3:18])[CH:11]=[CH:10]2)(=O)=O.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[Cl-].[Li+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:19][C:8]1[C:7]([CH:22]=[CH2:23])=[C:16]([CH3:17])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([CH3:18])=[N:13]2PdCl2(PPh3)2 (207 mg, 0.30 mmol) was added to a mixture of 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (5A) (1.13 g, 2.95 mmol), tributyl(vinyl)stannane (0.95 mL, 3.25 mmol) and lithium chloride (375 mg, 8.85 mmol) in DMF (30 mL). The reaction mixture was flushed with argon, heated at 80° C. for 4 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide 5B (678 mg, 88%). LCMS-ESI+ (m/z): 262.1, 264.1 (M+H)+.
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