Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C.C1(C)C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=15-Bromopyridin-2(1H)-one (1.04 g), (2-fluorophenyl)boronic acid (0.924 g), sodium carbonate (1.40 g), lithium chloride (0.560 g) and tetrakis(triphenylphosphine)palladium(0) (0.347 g) were suspended in a mixed solvent of toluene (26.4 mL), ethanol (6.6 mL) and water (6.6 mL), and the suspension was stirred at 100° C. for 17 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with brine, extracted with ethyl acetate, diluted with THF, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→ethyl acetate/methanol) to give the title compound (0.0563 g).
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