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

HRID 1888387
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HRID 1888387 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11
1,2-Dichloroethane
용매
HCID 8003Pentane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c5b17333aeb348b1a88657af373827cd
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501765B2

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