反应详情

250 mL of MeOH, 220 mL of 2N sodium carbonate (Na2CO3) solution, and 1.80 g (2.46 mmol) of PdCl2(dppf) are added to a solution of 59.5 g (201.0 mmol) of 5-bromo-2-[(tert-butyldimethylsilanyl)ethynyl]pyridine and 36.5 g (233.4 mmol) of 4-chlorophenylboric acid in 600 mL of 1,4-dioxane and the mixture is refluxed for 1 hour. The reaction mixture is evaporated down in vacuo and diluted with EtOAc. The organic phase is washed with water and semisaturated sodium bicarbonate (NaHCO3) solution, dried over sodium sulfate, and evaporated down in vacuo. The residue is purified by column chromatography (silica gel, Cyc/EtOAc 9:1). Yield: 38.5 g (58% of theoretical); C19H22ClNSi (M=327.923); calc.: molpeak (M+H)+: 328/330 (Cl); found: molpeak (M+H)+: 328/330 (Cl); Rf value: 0.60 (silica gel, Cyc/EtOAc 8:1).

1. temperaturethe mixture is refluxed for 1 hour
2. customThe reaction mixture is evaporated down in vacuo
3. additiondiluted with EtOAc
4. washThe organic phase is washed with water and semisaturated sodium bicarbonate (NaHCO3) solution
5. dry with materialdried over sodium sulfate
6. customevaporated down in vacuo
7. customThe residue is purified by column chromatography (silica gel, Cyc/EtOAc 9:1)