6-Amino-3-chloropyridazine → 6-Chloro-3-methyl-2-(trifluoromethyl)imidazo[1,2-b]pyridazine

HRID 1896355Notes

Reaction equation

HRID 1896355 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH:10]([CH3:17])[C:11](=O)[C:12]([F:15])([F:14])[F:13]>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH3:17])=[C:11]([C:12]([F:15])([F:14])[F:13])[N:8]=2)[N:7]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 27364103-Bromo-1,1,1-trifluorobutan-2-one

Product 1

HCID 536291536-Chloro-3-methyl-2-(trifluoromethyl)imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 6-chloro-3-aminopyridazine x34 (3.16 g, 1 eq, 24.2 mmol) and 3-bromo-1,1,1-trifluorobutan-2-one (5 g, 1 eq, 24.4 mmol) in 1,2-dimethoxyethane (100 ml) is refluxed during 17 hours. After cooling to room temperature and filtration, the solvent is removed under reduced pressure and the crude mixture is purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 98/2/0.2 (v/v/v)) leading to 6-chloro-3-methyl-2-(trifluoromethyl)imidazo[1,2-b]pyridazine x35.

Workup

  1. filtrationfiltration
  2. customthe solvent is removed under reduced pressure
  3. customthe crude mixture is purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 98/2/0.2 (v/v/v))

Sources & evidence

ORD record
ord-a836f299d7d346d0a3cf1a48d08a7d4c
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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