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

HRID 83497

反応式

HRID 83497 の反応式
[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

参加物

8

反応物 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 707251-Fluoro-3-iodobenzeneHCID 178425430HCID 178425430、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 14829Copper oxide触媒HCID 1140Toluene溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-be681fdb8c0f4f5e8dfdcac87443dbe7
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

関連ノート

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