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

HRID 83538

反応式

HRID 83538 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.[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

参加物

8

反応物 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 676731-Fluoro-2-iodobenzeneHCID 178425430HCID 178425430、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 178419072HCID 178419072、化合物触媒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 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-a21e600cd7d34c8eafc6b8fb94ebf901
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

関連ノート

読み込み中…