N-Iodosuccinimide → 3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine

HRID 425892Notes

Reaction equation

HRID 425892 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11].[I:20]N1C(=O)CCC1=O>C(#N)C.C(O)(=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[C:17]([I:20])[CH:18]=1)[CH3:11]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 211113963-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Product 1

HCID 211113953-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amineYield 50.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine (10.0 g, 33.2 mmol) in acetonitrile (600 mL) and acetic acid (120 mL) was added N-iodosuccinimide (11.2 g, 49.8 mmol). The mixture was stirred at room temperature for 4 hr and the reaction was quenched with Na2S2O5 solution. After evaporation, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N NaOH solution, brine, and dried over Na2SO4. The crude product was purified on a silica gel column to provide 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-iodo-pyridin-2-ylamine (7.1 g, 50% yield).MS m/z 427 [M+1]

Workup

  1. customthe reaction was quenched with Na2S2O5 solution
  2. customAfter evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 2N NaOH solution, brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-5ad33d42b25d43de8160b5c0dd1cf1fb
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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