Synthesis
General procedure: After evacuation under a standard cycle and backfilling with dry pure nitrogen, palladium catalyst (see Tables 1, 2, 3, and 4 for amounts), ligand (see Tables 1, 2, 3, and 4), N,N-dimethylpyridin-4-amine (DMAP, see Tables 1, 2, 3, and 4), and monoethyl malonate potassium salt (see Tables 1, 2, 3, and 4) were added sequentially to the oven-dried Schlenk tubes fitted with a magnetic stir bar. and Table 4), and monoethyl malonate potassium salt (see Tables 1, 2, 3, and 4 for amounts). Subsequently, the Schlenk tubes were evacuated and backfilled with argon, and this process was repeated three times. Under argon protection, 3-bromopyridine (see Tables 1, 2, 3, and 4 for amounts) and solvent (see Tables 1, 2, 3, and 4 for types and amounts) were added via syringe. The Schlenk tube was sealed and stirred for 10 minutes at room temperature. After that, the Schlenk tube was connected to an argon-filled Schlenk line and placed in an oil bath preheated to 140-150°C and the reaction was stirred for 20-25 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ether and the yield of ethyl 3-pyridylacetate was determined by gas chromatography using 1,3-dimethoxybenzene as an internal standard.
References
[1] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120
