[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[N:20]=1>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[Br:18][C:19]1[N:20]=[C:21]([C:4]2[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=2)[CH:22]=[CH:23][CH:24]=1A flask was charged with (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)boronic acid (80 mg, 0.52 mmol), potassium carbonate (217 mg, 1.57 mmol), and 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (19 mg, 0.026 mmol) and evacuated and purged with argon (5×). 2,6-Dibromopyridine (130 mg, 0.55 mmol) was placed into a separate flask and evacuated and backfilled with argon (3×). Degassed dimethylformamide (3.6 mL) was added to the vial containing 2,6-dibromopyridine and the solution was transferred to the flask containing the remainder of the reactants. The mixture was heated at 80° C. overnight, then cooled to room temperature, taken up in water, and extracted with ethyl acetate (2×). The ethyl acetate layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was purified via silica gel chromatography (0-5% methanol in ethyl acetate) to afford the title compound.
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