Sodium Iodide → 1-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-one

HRID 1892298Notes

Reaction equation

HRID 1892298 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[CH:9]N(C)C)=[CH:4][CH:3]=1.[Na+].[I-].Cl[CH2:16][C:17](=[O:19])[CH3:18]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]([C:17](=[O:19])[CH3:18])=[CH:9][N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 6802247[2-(6-Chloro-3-pyridazinyl)-2-azavinyl]dimethylamine

Product 1

HCID 132488051-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-oneYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N′-(6-chloro-pyridazin-3-yl)-N,N-dimethyl-formamidine (1.3 g, 7 mmol) in DMF (60 mL) was added NaI (1 g, 6.7 mmol) and chloroacetone (1 mL, 12.6 mmol). The mixture was heated at 80° C. overnight and concentrated under reduced pressure. The residue was purified by column chromatography to afford 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethanone (0.7 g) in 51% yield. 1H-NMR (400 MHz, CDCl3) δ ppm 8.42 (s, 1H), 8.05 (d, 1H), 7.31 (d, 1H), 2.77 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-589ebeeddd5f4230b2e7b964ab57023e
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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