Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC#N>[N:5]1[CH:6]=[CH:7][C:2]([CH:17]=[CH:16][C:15]([O:19][CH3:20])=[O:18])=[CH:3][CH:4]=1A mixture of 4-bromopyridine (40.6 g, 0.25 mmol), palladium acetate (1.16 g, 5.14 mmol), tri-(O-tolyl)phosphine (3.14 g, 10.3 mmol), CH3CN (129 mL), triethylamine (64.3 mL, 0.46 mmol) and methyl acrylate (46.8 mL, 0.514 mmol) was sealed in a bomb and placed in an oil bath at 120° C. for 4 hours. The mixture was cooled to 0° C., the bomb was vented, and the slurry thus obtained was partitioned between CH2Cl2 /water. The aqueous phase was separated, extracted with CH2Cl2 (2×200 mL) and the combined organic layers were dried over MgSO4. The solvent was removed in vacuo to afford 38 g of methyl 3-(4-pyridyl)propenoate.
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