N-bromobutanimide → 5-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amine

HRID 1809646Notes

Reaction equation

HRID 1809646 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1.[Br:16]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:16][C:13]1[CH:14]=[C:9]([O:8][C:7]2[CH:6]=[CH:5][N:4]=[N:3][C:2]=2[CH3:1])[C:10]([NH2:15])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 674859363-(3-Methylpyridazin-4-yloxy)pyridin-2-amine

Product 1

HCID 674853455-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(3-Methylpyridazin-4-yloxy)pyridin-2-amine (0.50 g, 2.5 mmol) was dissolved in DMF (7 mL). N-Bromosuccinimide (0.46 g, 2.6 mmol) was added and the solution stirred at ambient temperature for 5 minutes. The solution was diluted with water and filtered through celite (rinsing with chloroform). The solution was extracted with chloroform, dried (Na2SO4), filtered and concentrated. Flash chromatography gave 5-bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amine (0.66 g, 95%).

Workup

  1. filtrationfiltered through celite (rinsing with chloroform)
  2. extractionThe solution was extracted with chloroform
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f16f41b768c4d76a78711125687c369
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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