8-Hydroxyquinoline → 3-(2,5-Dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-1H-pyrazole

HRID 83497

반응식

HRID 83497 반응식
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=CC=2O)C=CC=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33](I)[CH:32]=1>CN1CCCC1=O.[Cu]=O.C1(C)C=CC=CC=1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([F:30])[CH:32]=3)[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 707251-Fluoro-3-iodobenzeneHCID 178425430HCID 178425430, 화합물

생성물 1

HCID 712877533-(2,5-Dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-1H-pyrazole

시약·촉매·용매 3

HCID 14829Copper oxide촉매HCID 1140Toluene용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole (6.8 g) in N-methyl-2-pyrrolidone (68 ml) were sequentially added cesium carbonate (27.4 g), 8-quinolinol (1.2 g), copper oxide (I) (0.6 g) and 1-fluoro-3-iodobenzene (7.4 ml), and the mixture was stirred at 110° C. for 2 hours. This reaction mixture was cooled to room temperature, and toluene (80 ml) was added thereto, and then the mixture was filtered through Celite. After adding a 1M aqueous solution of sodium hydroxide (80 ml) to the filtrate, the mixture was extracted with toluene. The resulting organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1) to give the titled compound (10.4 g).

후처리

  1. temperatureThis reaction mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. additionAfter adding a 1M aqueous solution of sodium hydroxide (80 ml) to the filtrate
  4. extractionthe mixture was extracted with toluene
  5. washThe resulting organic layer was sequentially washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-be681fdb8c0f4f5e8dfdcac87443dbe7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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