N-bromobutanimide → 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

HRID 1809169Notes

Reaction equation

HRID 1809169 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)Cl>[Br:11][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 102612868-Chloroimidazo[1,2-a]pyrazine

Product 1

HCID 100598493-Bromo-8-chloroimidazo[1,2-a]pyrazineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chloro-imidazo[1,2-a]pyrazine (1.53 g, 0.01 mol) in DCM (30 mL) is added N-bromosuccinimide (1.78 g, 0.01 mol) and the reaction is stirred at room temperature for 2 h. After this time the solution is washed with saturated aqueous solution of Na2CO3 (2×20 mL), dried (MgSO4), filtered and concentrated in vacuo to give 3-bromo-8-chloro-imidazo[1,2-a]pyrazine (2.11 g, 96%).

Workup

  1. washAfter this time the solution is washed with saturated aqueous solution of Na2CO3 (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf8a9a77aa594ef0b7433c4b0975d3af
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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