Sodium Bicarbonate → 6-Bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazine

HRID 2203025Notes

Reaction equation

HRID 2203025 reaction equation
[Br:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH:10]([CH3:16])[C:11]([CH:13]1[CH2:15][CH2:14]1)=O.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH3:16])=[C:11]([CH:13]3[CH2:15][CH2:14]3)[N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27947796-Bromopyridazin-3-amineHCID 450808052-Bromo-1-cyclopropylpropan-1-one

Product 1

HCID 896902906-Bromo-2-cyclopropyl-3-methylimidazo[1,2-b]pyridazineYield 75.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromopyridazin-3-amine (1.0 g) in DMA (10 ml) were added 2-bromo-1-cyclopropylpropan-1-one (2.04 g) and NaHCO3 (0.966 g) at room temperature, and the mixture was stirred at 80° C. for 16 h. The mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (1.10 g) as yellow crystals.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-6798e30b905a47f68c313087aa4add32
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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