反応 #61006

反応方程式

1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

imidazole

cesium carbonate

1,10-phenanthroline

→

title compound

収率 41.9%

1-{3-Fluoro-4-[4-(5-imidazol-1-yl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone

収率 41.9%

溶媒

dioxane

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   その他quenched with water/ethyl acetate
3. 3
   抽出The aqueous layer was extracted twice with ethylacetate
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   その他the solvent was removed in vacuo
7. 7
   その他The crude oil was chromatographed over silicagel

実験手順

In a tube were added successively 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (example BJ, 0.05 g, 0.1 mmol), imidazole (8.4 mg, 0.12 mmol), cesium carbonate (70 mg, 0.21 mmol), CuI (4 mg, 0.02 mmol), 1,10-phenanthroline (7.3 mg, 0.04 mmol) and dioxane (0.2 ml). The mixture was heated under argon at 120° C. for 12 hours. The reaction mixture was cooled to room temperature and quenched with water/ethyl acetate. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: CH2Cl2/methanol: 0-5% to provide the title compound as a brown solid (20 mg, 40%), MS (m/e): 478.4 (M+H, 100%)

出典