反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
产物
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 ethyl 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-(hydroxymethyl)cyclohexanecarboxylate (201 mg, 0.251 mmol), tributyl(1-ethoxyvinyl)stannane (0.255 mL, 0.754 mmol), Pd(PPh3)4 (29.0 g, 0.025 mmol) in dioxane was stirred at 100° C. under Ar2 for 16 h. The reaction mixture was passed through a short SiO2/KF (9:1) plug to remove majority of the Sn species, and then purified by a SiO2 column (0-30% EtOAc/Hexanes, Rf=0.7 in 50% EtOAc) to afford ethyl 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-(hydroxymethyl)cyclohexanecarboxylate as a pale yellow oil (167 mg). HPLC-MS TR=3.18 min (UV 254 nm, 5 min method); mass calculated for formula C41H62N6O6Si2 790.4, observed LCMS m/z 791.2 (M+H).
WORKUP
后处理
- customto remove majority of the Sn species
- custompurified by a SiO2 column (0-30% EtOAc/Hexanes, Rf=0.7 in 50% EtOAc)