Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:21][CH:20]=1
Methyl 2-chloroisonicotinate (300 mg, 1.75 mmol) obtained in Step 1 of Reference Example 5 was dissolved in toluene (3.5 mL), and the solution was added with palladium acetate (11.8 mg, 0.0525 mmol), 2,2′-bis(diphenylphosphino)-2,2′-binaphthyl (49.1 mg, 0.0788 mmol), cesium carbonate (798 mg, 2.45 mmol) and 4-fluorophenylboronic acid (294 mg, 2.10 mmol), followed by stirring at 100° C. for 1 hour under argon atmosphere. After an insoluble matter of the reaction mixture was filtered off, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95 to 10/90) to obtain Methyl 2-(4-fluorophenyl)isonicotinate (284 mg, 70%).
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