反应详情

温度

110 °C

To a stirred mixture of 4-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (VIII) (0.830 g, 2.22 mmol), 2-isopropyloxyphenylboronic acid (0.400 g, 2.22 mmol) in saturated sodium carbonate solution (10 ml) and 1,4-dioxane (10 ml) was added palladium(II) acetate (0.1 g, 0.44 mmol) followed by triphenylphosphine (0.11 g, 0.42 mmol) at room temperature under an atmosphere of nitrogen. The resulting mixture was heated to reflux at 110° C. for one hour and monitored by TLC. The reaction mixture was filtered through a celite bed and the filtrate was extracted with ethyl acetate (3×100 ml). The organic layers were separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel, elution with 50% ethyl acetate/n-hexanes) to afford 4-[6-(2-isopropoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XIII) (0.36 g, 37%) as a white solid.

1. temperatureThe resulting mixture was heated
2. filtrationThe reaction mixture was filtered through a celite bed
3. extractionthe filtrate was extracted with ethyl acetate (3×100 ml)
4. customThe organic layers were separated
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by flash column chromatography (silica gel, elution with 50% ethyl acetate/n-hexanes)