Bromine → 3-Bromo-6-chloroimidazo(1,2-b)pyridazine

HRID 2279062Notes

Reaction equation

HRID 2279062 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[CH:11][N:12]=2)[N:9]=1>C(O)(=O)C>[Br:1][C:10]1[N:8]2[N:9]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]2=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (3.8 mL, 74.19 mmol) was added dropwise to a solution of 6-chloroimidazo[1,2-b]pyridazine (Preparation 1a, 4.8 g, 31.06 mmol) in glacial acetic acid (80 mL) and the resulting mixture was stirred at ambient temperature for 20 minutes. The precipitate formed was collected by filtration, washed with diethyl ether several times and dried in vacuo. The solid obtained was partitioned between ethyl acetate and a saturated aqueous solution of potassium carbonate. The organic layer was separated and washed with a saturated aqueous solution of potassium carbonate, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude was then treated with pentane, filtered and the solid obtained was dried in vacuo to yield the title compound (6.6 g, 92%) as a pale yellow solid.

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether several times
  4. customdried in vacuo
  5. customThe solid obtained
  6. customwas partitioned between ethyl acetate
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of potassium carbonate
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent removed under reduced pressure
  11. additionThe crude was then treated with pentane
  12. filtrationfiltered
  13. customthe solid obtained
  14. customwas dried in vacuo

Sources & evidence

ORD record
ord-b7176bb650194315ae35075fbfe2f3bb
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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