반응 #219777

반응 방정식

N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

DMF

boron tribromide

→

solid

수율 45.0%

N-[5-Bromo-2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

수율 45.0%

용매

CH2Cl2

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise under nitrogen
2. 2
   기타art room temperature
3. 3
   기타Then the reaction mixture was quenched with methanol
4. 4
   workup.ADDITIONdiluted with water
5. 5
   추출extracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml)
6. 6
   건조The combined organic extracts were dried with sodium sulphate
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1)

실험 절차

To a stirred suspension of N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide (Example 32 iii)) (0.17 g, 0.36 mmol) in CH2Cl2 (5 ml) with some drops of DMF a solution of boron tribromide (BBr3) in dichloromethane (CH2Cl2) (1M, 1.08 mmol, 1.08 ml) was added dropwise under nitrogen. The stirring was continued overnight art room temperature. Then the reaction mixture was quenched with methanol, diluted with water and extracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml). The combined organic extracts were dried with sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1) to give a colourless solid (89 mg, 0.16 mmol, 45%).

출처