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

HRID 83922노트

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HRID 83922 반응식
Cl[CH2:2][C:3]1[N:4]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)([CH3:10])[CH3:9])=[CH:6][N:7]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=1[OH:37])[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=1[O:37][CH2:2][C:3]1[N:4]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)([CH3:9])[CH3:10])=[CH:6][N:7]=1)[C:30]([O:32][CH3:33])=[O:31]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 66619271Methyl 3-chloro-5-fluoro-4-hydroxybenzoateHCID 667400042-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

생성물 1

HCID 66740309methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate수율 68%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

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]+.

후처리

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. extractionextracted further with DCM
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe material was purified by chromatography (silica, 0-70% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-9e77f86e596142c1b1e3e0074338f36a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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