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 microwave vial was charged with 6-bromo-1,2-dimethyl-1H-benzo[d]imidazole (150 mg, 0.67 mmol), Bis(pinacolato)diboron (189 mg, 0.74 mmol), PdCl2(dppf).CH2Cl2 (55 mg, 0.07 mmol), then KOAc (221 mg, 2.25 mmol). The vial was flushed with argon, diluted with dioxane (3 mL), sealed, then heated to 100° C. for 45 minutes. The reaction mixture was allowed to cool to room temperature and then a portion of this cooled solution (1.0 mL, 0.22 mmol) was added to a vial that was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (55 mg, 0.10 mmol) and Pd(PPh3)4 (12 mg, 0.01 mmol). The mixture was diluted with dioxane (1.5 mL) and to this was added 2M aqueous K2CO3 (0.21 mL, 0.42 mmol). The vial was sealed, heated to 100° C. for 1 hour, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered through a small pad of silica gel, and concentrated in vacuo to afford the desired product. LCMS-ESI+: calc'd C31H33ClN3O3S: 562.2 (M+H+); Found: 562.3 (M+H+).
WORKUP
后处理
- customThe vial was flushed with argon
- additiondiluted with dioxane (3 mL)
- customsealed
- temperatureto cool to room temperature
- customThe vial was sealed
- temperatureheated to 100° C. for 1 hour
- temperatureto cool to room temperature
- dry with materialdried over Na2SO4
- filtrationfiltered through a small pad of silica gel
- concentrationconcentrated in vacuo