Ethyl Acetate → 3-Bromo-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 69163Notes

Reaction equation

HRID 69163 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.[Br:16]N1C(=O)CCC1=O.CCOC(C)=O>CN(C=O)C>[Br:16][C:13]1[N:11]2[N:12]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=[CH:9][C:10]2=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 686316286-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 686324863-Bromo-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Stage 8.2, 2.22 g, 11.1 mmol) was dissolved in DMF (33 mL) and cooled down to 0° C. with an ice-water bath. Then N-bromo-succinimide (2.3 g, 12.3 mmol) was added and the RM was stirred at the same temperature for 1 h45. It was then taken up with EtOAc and washed with a saturated solution of NaHCO3 and brine. The organic layer was dried over Na2SO4 and the solvent was removed. The residue was triturated with Et2O and the precipitate was filtered off to afford the title compound as a yellow solid (tR 1.3 min (conditions 2), MH+=278).

Workup

  1. washwashed with a saturated solution of NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed
  4. customThe residue was triturated with Et2O
  5. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-b6993c850b5e48109f2800ad5a0c28e2
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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