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
- 75 °C
PROCEDURE
实验过程
1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (265 mg, 625 μmol, see Example 53), 3-pyridylboronic acid (115 mg, 937 μmol), and tetrakis(triphenylphosphine)palladium (72 mg, 62 μmol) were mixed in dioxane (4 mL) in a microwave tube under a nitrogen atmosphere. 2M Na2CO3 (937 μL, 1874 μmol) was added via syringe, and the reaction mixture was stirred at 75° C. for 15 hours. The reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated in vacuo to give the crude product as a yellow solid. The crude product was purified by silica flash chromatography (0-10% EtOAc/DCM) to give the desired compound as an off-white solid (190 mg). MS (m/e)=423.2 (M+H)+.
WORKUP
后处理
- temperatureThe reaction mixture was cooled to room temperature
- custompartitioned between EtOAc and water
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give the crude product as a yellow solid
- customThe crude product was purified by silica flash chromatography (0-10% EtOAc/DCM)