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

HRID 2096275
Notes
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Reaction equation

HRID 2096275 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-994686d555cd4fa69de1aaab6d87a870
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450320B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes