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Azobisisobutyronitrile → 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-bromo-2-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester

HRID 1505851
ノート
印刷プレビュー

反応式

HRID 1505851 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[N:7]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:6]=1[CH3:24])=[O:4].C1C(=O)N([Br:32])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClCCCl.CCCCC>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[N:7]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:6]=1[CH2:24][Br:32])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 582665641H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-bromo-2-methyl-1-(phenylsulfonyl)-, methyl ester

生成物 1

HCID 582663771H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-bromo-2-(bromomethyl)-1-(phenylsulfonyl)-, methyl ester収率 94.2%

試薬・触媒・溶媒 2

HCID 11
1,2-Dichloroethane
溶媒
HCID 8003Pentane溶媒

実験手順

To a solution of 1-benzenesulfonyl-5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (0.42 g, 1.0 mmol) in 1,2-dichloroethane (9 mL) were added NBS (0.20 g, 1.1 mmol) and AIBN (30 mg, 0.2 mmol) and the reaction mixture was heated under reflux for 45 minutes. The reaction mixture was allowed to cool to ambient temperature and was diluted with pentane (4.0 mL), the solid was removed by filtration and the liquors were then concentrated in vacuo. The resultant residue was purified by chromatography (silica, 5 g cartridge, Si-SPE, 30-100% DCM in pentane) to afford the title compound as a white solid (0.46 g, 90%). LCMS (Method B): RT=4.55 min, M+H+=489.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. customthe solid was removed by filtration
  4. concentrationthe liquors were then concentrated in vacuo
  5. customThe resultant residue was purified by chromatography (silica, 5 g cartridge, Si-SPE, 30-100% DCM in pentane)

出典と根拠

ORDレコード
ord-db06d0bacfb044bda4ac6782303d0b4a
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09216980B2

反応ノート

読み込み中…

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