反応 #171104

反応方程式

2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

methyl 3-chloro-5-fluoro-4-hydroxybenzoate

potassium carbonate

18-crown-6

→

methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate

収率 68.0%

溶媒

CH3CN

反応条件

後処理

1. 1
   温度After cooling
2. 2
   ろ過the reaction mixture was filtered
3. 3
   抽出extracted further with DCM
4. 4
   洗浄The combined extracts were washed with brine
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The material was purified by chromatography (silica, 0-70% EtOAc/Hex)

実験手順

A mixture of 2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (154 mg, 0.39 mmol), methyl 3-chloro-5-fluoro-4-hydroxybenzoate (118 mg 0.57 mmol), potassium carbonate (79 mg, 0.57 mmol), and 18-crown-6 (11 mg, 0.04 mmol) in CH3CN (4 mL) was heated 8 h at 60° C. After cooling, the reaction mixture was filtered, combined with water and DCM, and then extracted further with DCM. The combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The material was purified by chromatography (silica, 0-70% EtOAc/Hex) to give methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate as a white solid (150 mg, 68% yield). MS (EI) m/z 567.3 [M+H]+.

出典