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Phosphorus trichloride → 4-[5-(4-Fluorophenyl)-1-methyl-2-phenyl-1h-imidazol-4-yl]pyridin-2(1h)-one

HRID 23526
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HRID 23526 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N+:10]([O-])[C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:4][CH:3]=1
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참가 물질

4

반응물 2

HCID 24387Phosphorus trichlorideHCID 695576504-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

생성물 1

HCID 225741694-[5-(4-Fluorophenyl)-1-methyl-2-phenyl-1h-imidazol-4-yl]pyridin-2(1h)-one수율 40.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
60 °C

실험 절차

To a solution of 4-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one of Step A (56 mg, 0.155 mmol) in CHCl3 (2 mL) was added phosphorous trichloride (16 μL, 0.186 mmol) dropwise at room temperature. The reaction mixture was heated at 60° C. for 2 hours, cooled, and poured into 1N NaOH/ice solution. The aqueous layer was extracted with CH2Cl2, and the combined organic extracts were washed with H2O followed by brine. After drying over Na2SO4, the solvent was removed in vacuo. The crude material was purified by preparative thin layer chromatography (1:10 MeOH:CH2Cl2 as an eluent) to obtain 21.8 mg of the title compound.

후처리

  1. temperaturecooled
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic extracts were washed with H2O
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude material was purified by preparative thin layer chromatography (1:10 MeOH

출처 및 근거

ORD 기록
ord-d536d149bf6e440b94ffa5ef2b01369e
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06852727B2

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