反应详情

温度

0 °C

2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (466.2 mg, 2.0 mmol) and cesium carbonate (782.0 mg, 2.4 mmol) were suspended in anhydrous acetonitrile (20 mL) and the mixture was cooled to 0° C. Methyl 3-(bromomethyl)-5-tert-butylthiophene-2-carboxylate (109c) (584.4 mg, 2.0 mmol) was then added. The resulting mixture was allowed to gradually warm to room temperature, then stirred at 40° C. overnight. The reaction mixture was filtered through Celite®, and the filtrate was concentrated. The residue was purified on silica eluted with a gradient of 0 to 10% Ethyl acetate in heptane to afford methyl 2-tert-butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylate (109d) (501.6 mg, 56%).

1. temperatureto gradually warm to room temperature
2. filtrationThe reaction mixture was filtered through Celite®
3. concentrationthe filtrate was concentrated
4. customThe residue was purified on silica
5. washeluted with a gradient of 0 to 10% Ethyl acetate in heptane