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Dimethylformamide → 1-(2-Iodobenzoyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

HRID 433067
ノート
印刷プレビュー

反応式

HRID 433067 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]#N)[C:6]([N+:12]([O-])=O)=[CH:5][CH:4]=1.[H-].[Na+].[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].CN([CH:30]=[O:31])C>>[I:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:12]1[C:6]2[C:7](=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]([CH:30]=[O:31])=[CH:10]1)=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 691122-Iodobenzoyl chlorideHCID 6395106-Methoxy-3-nitropyridine-2-acetonitrile

生成物 1

HCID 187582411-(2-Iodobenzoyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

反応条件

温度
0 °C

実験手順

Under an argon atmosphere, 0.56 mmol of the compound obtained in Step A are dissolved in 5 ml of DMF, and then 0.68 mmol of NaH are added at 0° C., over a period of 30 minutes. After 30 minutes' stirring at 0° C., 0.68 mmol of 2-iodobenzoyl chloride dissolved in 5 ml of DMF is added dropwise to the mixture. After 3 hours' stirring, the solvents are removed by evaporation and the residue is taken up in water and extracted with dichloromethane. After drying over magnesium sulphate and removal of the solvents by evaporation, the residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate) to yield the title compound.

後処理

  1. additionis added dropwise to the mixture
  2. stirringAfter 3 hours' stirring
  3. customthe solvents are removed by evaporation
  4. extractionextracted with dichloromethane
  5. dry with materialAfter drying over magnesium sulphate and removal of the solvents by evaporation
  6. customthe residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate)

出典と根拠

ORDレコード
ord-0ef1ca36a1514b65987adfd4ee1c2dc6
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06667304B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート