Iodine → 6-Bromo-2-iodopyridin-3-amine

HRID 1842034Notes

Reaction equation

HRID 1842034 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:8])=[N:6][CH:7]=1.[I:9]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[Br:8][C:5]1[N:6]=[C:7]([I:9])[C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 807IodineHCID 6428116-Bromopyridin-3-amine

Product 1

HCID 534011776-Bromo-2-iodopyridin-3-amineYield 89.2%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

5.0 g 5-Amino-2-bromopyridine were dissolved in 70 ml ethanol. 9.0 g silver sulfate and 7.33 g iodine were added. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue diluted with 500 ml ethyl acetate and filtered over a celite pad. The filtrate was washed with 200 ml saturated Na2S203 solution and water, dried over MgSO4 and then the solvent was removed in vacuo to obtain 7.7 g 6-Bromo-2-iodo-pyridin-3-ylamine.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with 500 ml ethyl acetate
  3. filtrationfiltered over a celite pad
  4. washThe filtrate was washed with 200 ml saturated Na2S203 solution and water
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0e25cf880a41421cb72b4c3519daac3d
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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