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 solution of 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (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 nitrogen, and heated at 80° C. for 4 hours. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, and dried over Na2SO4. Concentration and purification by flash column chromatography yielded 5-bromo-2,7-dimethyl-6-vinylquinoline. LCMS-ESI+ (m/z): [M+H]+ calc'd for C13H13BrN: 262.0; Found: 262.1.
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