反应详情

温度

75 °C

Cyclopropanecarboxylic acid (5-bromo-2-iodo-benzyl)-ethyl-amide (6.0 g, 14.7 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (5.2 g, 16.2 mmol), and potassium carbonate (5.09 g, 36.8 mmol) were combined in DME (50 mL) and water (20 mL) under nitrogen. The mixture was purged with nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.74 mmol) was added, and the reaction was heated to 75° C. The reaction was monitored by analytical LCMS and an additional portion of the boronic ester (0.500 g, 1.56 mmol) was added to push the reaction to completion. When the starting material was consumed, 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 (0-25% ethyl acetate in hexanes) to give the title compound.

1. customThe mixture was purged with nitrogen
2. customthe reaction to completion
3. customWhen the starting material was consumed
4. temperaturethe mixture was cooled to room temperature
5. additiondiluted with ethyl acetate and water
6. customThe aqueous layer was separated
7. extractionextracted with ethyl acetate
8. dry with materialthe combined organic layers were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by silica gel chromatography (0-25% ethyl acetate in hexanes)