反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 100 °C
PROCEDURE
实验过程
A mixture of 2-methoxyethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-methoxyethoxy)cyclohexanecarboxylate (300 mg, 0.343 mmol), tributyl(1-ethoxyvinyl)tin (0.348 mL, 1.03 mmol), Pd(PPh3)4 (39.6 mg, 0.034 mmol) in dioxane (3.5 mL) was stirred at 100° C. under Ar for 16 h. The reaction mixture was passed through a short SiO2/KF (9:1) plug (eluting with EtOAc) to remove the majority of Tin species. After evaporating, the crude product was purified by a SiO2 column (0-30%, EtOAc/Hexanes, Rf=0.65 in 50% EtOAc) to afford 2-methoxyethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-methoxyethoxy)cyclohexanecarboxylate as a pale yellow oil (258 mg, 87%).
WORKUP
后处理
- washThe reaction mixture was passed through a short SiO2/KF (9:1) plug (eluting with EtOAc)
- customto remove the majority of Tin species
- customAfter evaporating
- customthe crude product was purified by a SiO2 column (0-30%, EtOAc/Hexanes, Rf=0.65 in 50% EtOAc)