Azobisisobutyronitrile → 3-(Bromomethyl)-6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazine

HRID 1926730Notes

Reaction equation

HRID 1926730 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:15])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[N:7]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(#N)C>[Br:16][CH2:15][C:8]1[N:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 536291536-Chloro-3-methyl-2-(trifluoromethyl)imidazo[1,2-b]pyridazine

Product 1

HCID 536291543-(Bromomethyl)-6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazineYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-3-methyl-2-(trifluoromethyl)imidazo[1,2-b]pyridazine x35 (3.45 g, 1 eq, 14.64 mmol), N-bromosuccinimide (NBS; 2.87 g, 1.1 eq, 16.11 mmol) and azo-bis-iso-butyronitrile (AIBN; 240 mg, 0.1 eq, 1.5 mmol) in acetonitrile (50 ml) is refluxed for 2 hours. After cooling to room temperature, the solvent is removed under reduced pressure and the crude product is purified by preparative chromatography on silicagel (CH2Cl2) affording 3-(bromomethyl)-6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazine x36.

Workup

  1. temperatureis refluxed for 2 hours
  2. customthe solvent is removed under reduced pressure
  3. customthe crude product is purified by preparative chromatography on silicagel (CH2Cl2)

Sources & evidence

ORD record
ord-d21027511739422a97c37c774559cbfd
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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