N-bromobutanimide → 3-Bromo-6,8-dimethylimidazo[1,2-b]pyridazine

HRID 1904530Notes

Reaction equation

HRID 1904530 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[Br:12]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:12][C:8]1[N:6]2[N:7]=[C:2]([CH3:1])[CH:3]=[C:4]([CH3:11])[C:5]2=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 147503576,8-Dimethylimidazo[1,2-b]pyridazine

Product 1

HCID 147503563-Bromo-6,8-dimethylimidazo[1,2-b]pyridazineYield 83.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.63 g (24.7 mmol) of 6,8-dimethylimidazo[1,2-b]pyridazine in 25 mL of chloroform was added 4.84 g (27.2 mmol) of N-bromosuccinimide. After 2 h, 1 mL of a saturated aqueous solution of sodium bicarbonate was added. The layers were separated. The organic layer was dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by flash chromatography to give 4.66 g of the title compound as a white solid, m.p. 137°-139° C.

Workup

  1. customThe layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed with a rotary evaporator
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-deac443450254f8daf47a72e6367aa4d
Source dataset
uspto-grants-1989_06
Patent number
US04838925

Reaction notes

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