N-bromobutanimide → 3,6,8-Tribromoimidazo[1,2-a]pyrazine

HRID 1809198Notes

Reaction equation

HRID 1809198 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[N:11]=[C:12]([Br:19])[C:13]2[N:14]([CH:16]=[CH:17][N:18]=2)[CH:15]=1>ClCCl>[Br:1][C:16]1[N:14]2[CH:15]=[C:10]([Br:9])[N:11]=[C:12]([Br:19])[C:13]2=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 142076223,6,8-Tribromoimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-bromosuccinimide (1.81 g, 10.15 mmol) was added to a solution of 6,8-Dibromo-imidazo[1,2-a]pyrazine (2.0 g, 10.15 mmol) in dichloromethane (40 ml). The reaction was stirred at room temperature over night then diluted with dichloromethane (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (2×50 ml) and brine (50 ml). The organic layer was dried (MgSO4), filtered and concentrated in vaccuo. The product, 3,6,8-Tribromo-imidazo[1,2-a]pyrazine was obtained as a pink solid (2.77 g), sufficiently pure to be used in subsequent reactions.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate (2×50 ml) and brine (50 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-0fb4b0376bbf47478e875a3846773a01
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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