Br[C:2]1[CH:12]=[N:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(#N)C>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:2]2[CH:12]=[N:11][C:5]3[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=3[CH:3]=2)[CH:14]=1
To 1.6 ml of acetonitrile/0.4 ml of distilled water, 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2-one (100 mg, 0.436 mmol), 3-pyridine boronic acid (29.5 mg, 0.240 mmol), palladium acetate (4.9 mg, 0.0218 mmol), triphenylphosphine (11.4 mg, 0.0436 mmol) and potassium carbonate (45.2 mg, 0.327 mmol) were added and then stirred at 1000 for 10 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=50:1. The fractions containing the product were collected and evaporated to obtain 7-pyridin-3-yl-1H-pyrido[2,3-b][1,4]oxazin-2-one as brown oil (60 mg, 60%).
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