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

HRID 83538

반응식

HRID 83538 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.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1I.N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[F:13])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 676731-Fluoro-2-iodobenzeneHCID 178425430HCID 178425430, 화합물

생성물 1

HCID 866803713-(2,5-Dimethylpyrrol-1-yl)-1-(2-fluorophenyl)-1H-pyrazole

시약·촉매·용매 3

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

반응 조건

온도
110 °C

실험 절차

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole (1.00 g) prepared according to the same procedures as Preparation 4 in N-methylpyrrolidone (10 ml) were sequentially added 1-fluoro-2-iodobenzene (1.08 ml), copper (I) oxide (89 mg), 8-quinolinol (180 mg) and cesium carbonate (4.04 g) at room temperature, and the mixture was stirred at 110° C. for 3 hours. This reaction mixture was cooled to room temperature, and then toluene was added thereto, and the mixture was filtered through Celite. The filtrate was sequentially washed with a 2N aqueous solution of sodium hydroxide, water and 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 10/1) to give the titled compound (1.19 g).

후처리

  1. customat room temperature
  2. temperatureThis reaction mixture was cooled to room temperature
  3. filtrationthe mixture was filtered through Celite
  4. washThe filtrate was sequentially washed with a 2N aqueous solution of sodium hydroxide, water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 10/1)

출처 및 근거

ORD 기록
ord-a21e600cd7d34c8eafc6b8fb94ebf901
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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