Dimethylformamide → 5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole

HRID 1466478ノート

反応式

HRID 1466478 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([Cl:19])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:9]2)([O-:3])=[O:2].P(Cl)(Cl)(OCl)=O.CN([CH:29]=[O:30])C>ClCCl>[Cl:19][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:9]2[CH:29]=[O:30]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 684721085-chloro-7-nitro-2-phenyl-1H-indoleHCID 86587839Phosphoryloxychloride

生成物 1

HCID 866438345-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole収率 45.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

7-Nitro-5-chloro-2-phenyl-1H-indole (1.0 g, 3.67 mmol) prepared in Preparation 26 was dissolved in dichloromethane (20 mL). Phosphoryloxychloride (0.84 g, 5.50 mmol) and DMF (0.80 g, 11.01 mmol) were added in drops thereto at 0° C., and the mixture was stirred for 6 h at room temperature. After completion of the reaction, the reaction was quenched by saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (0.5 g, Yield 45%).

後処理

  1. customAfter completion of the reaction
  2. customthe reaction was quenched by saturated aqueous sodium hydrogen carbonate solution
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-d21f37f80e3044ca96c055590a9f99ab
出典データセット
uspto-grants-2015_04
特許番号
US09000028B2

反応ノート

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