Acetic Anhydride → N-(6-Iodoimidazo[1,2-A]pyridin-2-YL)acetamide

HRID 1372487Notes

Reaction equation

HRID 1372487 reaction equation
[C:1]([CH2:4][N:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][CH:6]1[NH:12]S(C1C=CC(C)=CC=1)(=O)=O)(=O)[NH2:2].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[I:11][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH:4]=[C:1]([NH:2][C:23](=[O:25])[CH3:24])[N:12]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 210717081-(Carbamylmethyl)-5-iodo-2-(p-toluenesulfonamido)pyridine

Product 1

HCID 58779346N-(6-Iodoimidazo[1,2-A]pyridin-2-YL)acetamide

Procedure

A mixture of the product from Step B (300 mg, 0.70 mmol) and 1.0 mL of acetic anhydride was warmed at reflux for 2.5 h. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the ethyl acetate layer was washed sequentially with saturated aqueous sodium bicarbonate solution and saturated aqueous brine, dried (magnesium sulfate) and concentrated under reduced pressure. The crude residue was purified by preparative thin-layer chromatography (silica gel, 7% methanol/dichloromethane) to afford the title compound as a pale yellow powder. LC/MS 301.9 (M+1).

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 2.5 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe ethyl acetate layer was washed sequentially with saturated aqueous sodium bicarbonate solution and saturated aqueous brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by preparative thin-layer chromatography (silica gel, 7% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c4917fdd990d4f7ea03e1d976665f036
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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