Chloroform → N-(6-chloro-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162491Notes

Reaction equation

HRID 1162491 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[N:14]=2)[N:11]=1.C1C(=O)N([I:26])C(=O)C1>O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([I:26])=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[N:14]=2)[N:11]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 120273N-IodosuccinimideHCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 57749438N-(6-chloro-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamideYield 83.41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a CHCl3 (20 mL) solution of N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (320.4 mg, 1521 μmol) was added n-iodosuccinimide (167.4 μl, 1673 μmol) as a solid in a single portion. The solution was maintained at rt for 20 min, then poured into water. The resulting mixture was extracted with CH2Cl2 (1×50 mL). The layers were separated and the organic layer was washed with saturated aqueous Na2S2O3 (1×20 mL) and brine (1×10 mL). The organic layer was dried (Na2SO4) and concentrated for purification by MPLC (CombiFlash® Companion®, Teledyne Isco, Lincoln, Nebr.). The residue was taken up in minimal CH2Cl2/MeOH and absorbed onto a 25 g silica loading cartridge and passed through a Redi-Sep® pre-packed silica gel column (80 g) (Teledyne Isco, Lincoln, Nebr.) using a gradient of 1% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2 to afford N-(6-chloro-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (427.0 mg, 83.41% yield) as a grey solid. LCMS (ESI positive ionization) m/z: 337.2 (M+1).

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2 (1×50 mL)
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated aqueous Na2S2O3 (1×20 mL) and brine (1×10 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated for purification by MPLC (CombiFlash® Companion®, Teledyne Isco, Lincoln, Nebr.)
  6. customabsorbed onto a 25 g silica loading cartridge

Sources & evidence

ORD record
ord-2b8c22e265c44e529879572e10170c81
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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