[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9](Br)=[CH:10][CH:11]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1A mixture of 2980 mg (12.31 mmol) of 3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 2067 mg (14.77 mmol) of 4-fluorophenylboronic acid, 138.2 mg (0.61 mmol) of palladium(II)acetate, 322.9 mg (1.23 mmol) of triphenylphosphane and 14.7 ml of a 1M sodium carbonate solution in 73 ml of toluene and 20 ml of ethanol was heated under reflux for 1.5 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The organic phases were evaporated and residue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 2.4 g (76%).
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