8-Hydroxyquinoline → 1-(4-Chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole

HRID 83533

반응식

HRID 83533 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.[Cl:30][C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1>CN1CCCC1=O.[Cu-]=O.C1(C)C=CC=CC=1>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:10]2[CH:11]=[CH:12][C:8]([N:3]3[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]3[CH3:7])=[N:9]2)=[CH:33][CH:32]=1

참가 물질

8

반응물 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 178425430HCID 178425430, 화합물

생성물 1

HCID 866803671-(4-Chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole수율 96.5%

시약·촉매·용매 3

HCID 178419072HCID 178419072, 화합물촉매HCID 1140Toluene용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

Under argon atmosphere, to a solution of 3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole (3.06 g) prepared according to the same procedures as Preparation 4 in N-methylpyrrolidone (31 ml) were sequentially added cesium carbonate (12.37 g), 8-quinolinol (0.55 g), copper (I) oxide (0.27 g) and 1-chloro-4-iodobenzene (6.79 g) at room temperature, the mixture was stirred at 110° C. for 2 hours. This reaction mixture was cooled to room temperature, and then toluene (30 ml) was added thereto, the mixture was filtered through Celite, and further subjected to elution with toluene. The filtrate was sequentially washed with a 1N aqueous solution of sodium hydroxide, water, a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 9/1) to give the titled compound (4.98 g).

후처리

  1. customat room temperature
  2. temperatureThis reaction mixture was cooled to room temperature
  3. filtrationthe mixture was filtered through Celite
  4. washfurther subjected to elution with toluene
  5. washThe filtrate was sequentially washed with a 1N aqueous solution of sodium hydroxide, 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=1/0 to 9/1)

출처 및 근거

ORD 기록
ord-7b4191a76f0643c9b6f8e47b5d240bc2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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