Sodium Thiosulfate → 6-Chloro-2-(4-fluorophenyl)-3-iodoimidazo[1,2-b]pyridazine
Reaction equation
[I:1]Cl.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:12]=2)[N:9]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([I:1])=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[N:12]=2)[N:9]=1Participants
Procedure
A solution of 6.61 g (40.9 mmol) of iodine monochloride in 40 ml of chloroform is added in a rapid dropwise manner to a solution, cooled to 0° C., of 5.20 g (21.0 mmol) of 6-chloro-2-(4-fluorophenyl)imidazo[1,2-b]pyridazine (CAS number: 244081-70-7) in 130 ml of chloroform. After returning to ambient temperature and after stirring for 4 hours, the mixture is treated with a 5% aqueous solution of sodium thiosulphate. The product is extracted with dichloromethane, the organic phase is dried by filtration over a hydrophobic filtration cartridge and concentrated under reduced pressure. The residue is triturated in acetonitrile, the solid is isolated after filtration and rinsing with diisopropyl ether. 5.7 g of beige powder are isolated after drying under vacuum.
Workup
- customAfter returning to ambient temperature
- extractionThe product is extracted with dichloromethane
- customthe organic phase is dried by filtration over a hydrophobic filtration cartridge
- concentrationconcentrated under reduced pressure
- customThe residue is triturated in acetonitrile
- customthe solid is isolated
- filtrationafter filtration
- washrinsing with diisopropyl ether
Sources & evidence
- ORD record
- ord-8a15e145b27f4673a468f9f43dc9cbe5
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546395B2
Reaction notes
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