Hydrogen Bromide → HCID 58046377, compound

HRID 2046419Notes

Reaction equation

HRID 2046419 reaction equation
[N:1]1[CH:2]=[C:3]([C:10](=[O:12])[CH3:11])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.[BrH:13].[Br:14]Br>C(O)(=O)C>[Br:13][CH:11]([Br:14])[C:10]([C:3]1[N:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:9]2=[N:1][CH:2]=1)=[O:12]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 24408Bromine2×HCID 450861961-(Imidazo[1,2-b]pyridazin-3-yl)ethan-1-one

Product 1

HCID 58046377HCID 58046377, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
60 °C

Procedure

1-(Imidazo[1,2-b]pyridazin-3-yl)ethanone (502 mg, 3.11 mmol) was dissolved in acetic acid (7.8 mL) and 33% HBr in acetic acid (0.564 mL, 3.11 mmol) was added. Bromine (0.177 mL, 3.43 mmol) was added and the solution stirred at 60° C. for 1.5 h. After stirring for 1.5 h, added more bromine (0.08 mL, 1.56 mmol) and 33% HBr in acetic acid (0.282 mL, 1.56 mmol). The solution was stirred at 60° C. for 3 h. The solution was then cooled to room temperature and quenched with 10% aqueous sodium thiosulfate. The aqueous layer was extracted with dichloromethane (×3). The organic layers were combined and washed with aqueous saturated sodium bicarbonate. The organic layer was collected and dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken on to the next step without further purification. 1H NMR (500 MHz, CD3SOCD3) δ 8.88 (d, 1H); 8.83 (s, 1H); 8.40 (d, 1H); 7.66 (s, 1H); 7.61 (dd, 1H). LRMS (APCI) calc'd for (C8H5Br2N3O) [M+H]+, 317.9. found 317.9.

Workup

  1. stirringAfter stirring for 1.5 h
  2. stirringThe solution was stirred at 60° C. for 3 h
  3. temperatureThe solution was then cooled to room temperature
  4. customquenched with 10% aqueous sodium thiosulfate
  5. extractionThe aqueous layer was extracted with dichloromethane (×3)
  6. washwashed with aqueous saturated sodium bicarbonate
  7. customThe organic layer was collected
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was taken on to the next step without further purification

Sources & evidence

ORD record
ord-799c2b2708b940ef9f7e5cb5df7aaa49
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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