Dimethylformamide → Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

HRID 1188881ノート

反応式

HRID 1188881 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.Cl.Cl[CH2:29][C:30]1[N:31]([CH3:35])[CH:32]=[CH:33][N:34]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCCCCC.C(OCC)(=O)C.O>[CH3:35][N:31]1[CH:32]=[CH:33][N:34]=[C:30]1[CH2:29][O:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 66726144Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

生成物 1

HCID 66898045Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate収率 57.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (100 mg), 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (50 mg), potassium carbonate (83 mg) and N,N-dimethylformamide (20 mL) was stirred at 50° C. for 3 hr. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column to chromatography (ethyl acetate:hexane=60:40 to 100:0, volume ratio) to give the title compound (72 mg, yield 57%) as a white solid. The white solid was recrystallized from ethyl acetate-hexane to give colorless crystals. melting point 91-92° C.

後処理

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

出典と根拠

ORDレコード
ord-a6c7391b449848959935877ceaafd8b5
出典データセット
uspto-grants-2014_03
特許番号
US08673942B2

反応ノート

読み込み中…