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Benzenesulfonyl chloride → 7-bromo-7-(phenylsulfonyl)-5H-pyrrolo[3,2-b]pyrazine

HRID 2096275
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인쇄 미리보기

반응식

HRID 2096275 반응식
[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:5]2[NH:4][CH:3]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:1][C:2]1([S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])[C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:5]2[NH:4][CH2:3]1
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참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 122071933-Bromo-4,7-diazaindole

생성물 1

HCID 674408937-bromo-7-(phenylsulfonyl)-5H-pyrrolo[3,2-b]pyrazine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A solution of 7-bromo-5H-pyrrolo[3,2-b]pyrazine (1 g, 5.05 mmol) in N,N-dimethylformamide (10 ml) was cooled at 0° C., and sodium hydride (167 mg, 5.55 mmol) was added in several portions. After stirring at 0° C. for 30 minutes, benzenesulfonyl chloride (980 mg, 5.55 mmol) was added via syringe. The mixture was allowed to warm up to room temperature and stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the title compound. MS (DCI/NH3) m/z 339 (M+H)+.

후처리

  1. temperatureto warm up to room temperature
  2. stirringstirred for 4 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and brine
  4. washThe organic phase was washed with brine
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-994686d555cd4fa69de1aaab6d87a870
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450320B2

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