Chlorosuccinimide → 2-Bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazine

HRID 905999Notes

Reaction equation

HRID 905999 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C1C(=O)N([Cl:18])C(=O)C1>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([Cl:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 401522632-Bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazineYield 141%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1.8 g, 9.09 mmol) in 18 mL of DCM and 18 mL of DMF was added NCS (1.46 g, 10.9 mmol) at RT. The reaction mixture was stirred at RT overnight, then partitioned between EtOAc and brine. The organic layer was dried (MgSO4) concentrated to give 2.98 g of impure 2-bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazine as a yellow oil which was used for the next step without any purification.

Workup

  1. custompartitioned between EtOAc and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d4af79e4c11c43669e63e23be8e11efa
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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