Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][CH3:10].[B:11]1(B2OC(C)(C)C(C)(C)O2)[O:15]C(C)(C)C(C)(C)[O:12]1.C([O-])(=O)C.[K+]>O1CCOCC1.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.Cl[Pd]Cl.[Fe+2]>[CH3:10][O:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[B:11]([OH:15])[OH:12]A mixture of 4-bromo-3-methoxypyridine hydrochloride (0.34 g, 1.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.13 g, 0.16 mmol), bis(pinacolato)diboron (0.47 g, 1.85 mmol), and potassium acetate (0.75 g, 7.7 mmol) in dry 1,4-dioxane (6.0 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 19 h, the reaction was cooled to rt then filtered. After concentration, the residue was identified as 3-methoxypyridin-4-ylboronic acid that was used without purification.
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