N-bromobutanimide → HCID 58337160, compound

HRID 1809187Notes

Reaction equation

HRID 1809187 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[N:12]([CH:17]=[CH:18][N:19]=2)[C:13]([CH3:16])=[CH:14][N:15]=1>C(Cl)Cl>[Br:1][C:17]1[N:12]2[C:13]([CH3:16])=[CH:14][N:15]=[C:10]([Cl:9])[C:11]2=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10012287HCID 10012287, compound

Product 1

HCID 58337160HCID 58337160, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-bromosuccinimide (348 mg, 1.96 mmol) is added to a solution of 8-chloro-5-methyl-imidazo[1,2-a]pyrazine (327 mg, 1.98 mmol) in DCM (6 mL) and the reaction stirred at room temperature for 2 h. Once the reaction is finished the reaction mixture is diluted with DCM and washed twice with 4 mL of Na2CO3 sat., dried (MgSO4), filtered and concentrated in vacuo to give a crude mixture that is purified by column chromatography using a gradient of (Pet.Ether40-60/AcOEt: 9/1 to 7/3) to give 3-Bromo-8-chloro-5-methyl-imidazo[1,2-a]pyrazine as a brown solid (335 mg, 69%).

Workup

  1. washwashed twice with 4 mL of Na2CO3 sat.
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude mixture that
  6. customis purified by column chromatography

Sources & evidence

ORD record
ord-f65d2b0baf6e4e82835dd1eac1bd2133
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

Loading…