N-Iodosuccinimide → 6-Chloro-3-iodoimidazo[1,2-b]pyridazine

HRID 2205194Notes

Reaction equation

HRID 2205194 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[I:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([I:11])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 532498976-Chloro-3-iodoimidazo[1,2-b]pyridazineYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

6-chloroimidazo[1,2-b]pyridazine (2.0 g, 13.0 mmol, 1.0 equiv) in chloroform (20 mL) at room temperature was added N-iodosuccinimide (2.9 g, 13.0 mmol, 1.0 equiv) then stirred vigorously overnight. The reaction mixture was diluted in water and extracted with ethyl acetate. Purification using column chromatography gave 3.3 g of the yellow solid, 90%: 1H NMR δ 8.21 (d, J=7.6 Hz, 1H), 7.96 (s, 1H), 7.41 (d, J=7.6 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. customPurification

Sources & evidence

ORD record
ord-4e5dce4404514e6b9c769ccd44b63504
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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