Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C(B(CC)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.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>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=[CH:6][CH:5]=13-bromo anisole (17.4 g, 93.03 mmol) was dissolved in 650 mL tetrahydrofuran and 210 mL water in a 2 L round bottom flask equipped with a magnetic stirrer. Diethyl-(3-pyridyl)borane (15.73 g, 106.99 mmol), sodium carbonate (44.4 g, 418.64 mmol) and dichlorobis(triphenylphosphine)palladium (II) (9.8 g, 13.95 mmol) were added and the mixture heated at reflux for 4 h then cooled to ambient temperature. The mixture was diluted with 300 mL water and extracted with diethyl ether (2×300 mL). The extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was purified by flash chromatography (1:1 ethyl acetate/hexanes). Product fractions were concentrated under reduced pressure to yield 17.75 g (99%) of the desired compound as a pale yellow oil.
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