反应详情

250 mL of MeOH, 220 mL of 2N sodium carbonate solution, and 1.80 g (2.46 mmol) of PdCl2(dppf) were 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 was refluxed for 1 hour. The reaction mixture was evaporated down in vacuo and diluted with EtOAc. The organic phase was washed with water and semisaturated sodium bicarbonate solution, dried over sodium sulfate and evaporated down in vacuo. The residue was 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 was refluxed for 1 hour
2. customThe reaction mixture was evaporated down in vacuo
3. additiondiluted with EtOAc
4. washThe organic phase was washed with water and semisaturated sodium bicarbonate solution
5. dry with materialdried over sodium sulfate
6. customevaporated down in vacuo
7. customThe residue was purified by column chromatography (silica gel, cyc/EtOAc 9:1)