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
- 80 °C
PROCEDURE
实验过程
To a solution of (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate (0.25 g, 0.428 mmol, 1 equiv) and (S)-tributyl(2,4-difluoro-6-(pent-4-en-2-yloxy)phenyl)stannane (0.25 g, 0.513 mmol, 1.2 equiv) in DMF (2 mL, sparged with nitrogen for 10 min) was added Pd(PPh3)4 (49 mg, 0.043 mmol, 0.1 equiv), CsF (195 mg, 1.28 mmol, 3 equiv), and CuI (20 mg, 0.107 mmol, 0.25 equiv). The reaction was heated at 80° C. for 2 h. After 2 h, more stannane (300 mg) was added. Stir for 2 h and remove from heat. Upon cooling to ambient temperature, the reaction was diluted with EtOAc, washed with water, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (160 mg, 53%) as a film. LCMS (ESI, M+1): 702.25.
WORKUP
后处理
- customremove
- temperaturefrom heat
- temperatureUpon cooling to ambient temperature
- additionthe reaction was diluted with EtOAc
- washwashed with water
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography (0-100% EtOAc [2% TEA]/hexane)