Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[Cs+].[Cs+].[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].Cl[Cu]>[N:6]1[C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=[C:2]([C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[CH:7]=1
Into a solution of tert-butyl 5-bromopicolinate (3.5 g, 13.56 mmol) in DMF (40 ml) Pd(OAc)2 (0.152 g, 0.68 mmol), dppf (0.753 g, 1.37 mmol), CuCl (1.4 g, 13.57 mmol), Cs2CO3 (8.9 g, 27.13 mmol) and pyridin-3-yl boronic acid (3.4 g, 27.13 mmol) were added under inert atmosphere. The reaction mixture was stirred at 110° C. overnight and diluted with H2O. The mixture was filtered through a celite bed, and the filtrate was extracted with EtOAc. The organic layer was concentrated. Yield 1.75 g. 1H-NMR (400 MHz; CDCl3): δ 1.67 (s, 9H), 7.43-7.47 (m, 1H), 7.91 (d, J=8.0 Hz, 1H), 8.01 (dd, 1H), 8.17 (d, 1H), 8.70 (dd, 1H), 8.88 (d, 1H), 8.97 (d, 1H).
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