反应 #1712848

反应方程式

5-Bromo-2-ethoxypyridine

potassium carbonate

[2′-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-yl]-acetic acid ethyl ester

→

title compound

[2′-[(tert-Butoxycarbonyl-ethyl-amino)-methyl]-4′-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

溶剂

ethyl acetate

water

DME

water

反应条件

后处理

1. 1
   其他The mixture was purged with nitrogen
2. 2
   温度the mixture was cooled to room temperature
3. 3
   其他The aqueous layer was separated
4. 4
   萃取extracted with ethyl acetate
5. 5
   干燥the combined organic layers were dried over magnesium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他The residue was purified by silica gel chromatography (0-40% ethyl acetate in hexanes)

实验过程

5-Bromo-2-ethoxypyridine (0.235 g, 1.16 mmol), [2′-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-yl]-acetic acid ethyl ester (0.500 g, 0.903 mmol), and potassium carbonate (0.313 g, 2.3 mmol) were combined in DME (5 mL) and water (2.5 mL) under nitrogen. The mixture was purged with nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (0.052 g, 0.045 mmol) was added, and the reaction was heated to 85° C. for 6 hours. Once no starting material was seen by analytical LCMS, the mixture was cooled to room temperature and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-40% ethyl acetate in hexanes) to give the title compound.

来源