Sodium hydride → HCID 59304979、化合物

HRID 2240217ノート

反応式

HRID 2240217 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH2:15]C)=[O:13].[H-].[Na+].[Cl:19][C:20]1[N:25]=[C:24]2[N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:28][C:23]2=[C:22]([N+]([O-])=O)[CH:21]=1>CN(C=O)C>[Cl:19][C:20]1[N:25]=[C:24]2[N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:28][C:23]2=[C:22]([CH:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[F:1])[C:12]([O:14][CH3:15])=[O:13])[CH:21]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 469416086-Chloro-4-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridineHCID 56776686Ethyl (2-fluoro-4-nitrophenyl)acetate

生成物 1

HCID 59304979HCID 59304979、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

908 mg (4.26 mmol) of ethyl (2-fluoro-4-nitrophenyl)acetate are dissolved in 10 ml of DMF, and 170 mg (4.26 mmol) of sodium hydride (60% in mineral oil) are added. The mixture is stirred at RT for 30 min, and 698 mg (2.13 mmol) of 6-chloro-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine are then added. The mixture is heated at 70° C. for 2 hours and then stirred into ice-water and extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: dichloromethane/pentane 2:1).

後処理

  1. temperatureThe mixture is heated at 70° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by chromatography on silica gel (mobile phase: dichloromethane/pentane 2:1)

出典と根拠

ORDレコード
ord-d733d2109d7d4021b5c71a5315044115
出典データセット
uspto-grants-2010_05
特許番号
US07723347B2

反応ノート

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