Iodine → 2-Iodo-6-(trifluoromethyl)pyridin-3-amine

HRID 1690055Notes

Reaction equation

HRID 1690055 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:3][C:4]1[C:5]([I:1])=[N:6][C:7]([C:10]([F:13])([F:11])[F:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 27377445-Amino-2-(trifluoromethyl)pyridine

Product 1

HCID 534254792-Iodo-6-(trifluoromethyl)pyridin-3-amineYield 65.8%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

1.56 g (6.17 mmol) of iodine is added, in several portions, to a mixture, stirred under argon at 20° C., of 1 g (6.17 mmol) of 3-amino-6-trifluoromethylpyridine and 1.25 g (6.17 mmol) of silver sulfate in 40 mL of ethanol. Stirring is maintained for 18 hours. The insoluble matter is removed by filtration and is washed with ethanol, the filtrate is concentrated at reduced pressure, and the residue is taken up in 100 mL of dichloromethane. The organic phase is washed successively with 20 mL of 5% aqueous solution of sodium hydroxide, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride, dried over sodium sulfate, concentrated at reduced pressure, and then purified by chromatography on a silica column (eluents: heptane-ethyl acetate). In this way we isolate 1.17 g of the expected product, which is used as it is in the rest of the synthesis.

Workup

  1. temperatureis maintained for 18 hours
  2. customThe insoluble matter is removed by filtration
  3. washis washed with ethanol
  4. concentrationthe filtrate is concentrated at reduced pressure
  5. washThe organic phase is washed successively with 20 mL of 5% aqueous solution of sodium hydroxide, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. custompurified by chromatography on a silica column (eluents: heptane-ethyl acetate)

Sources & evidence

ORD record
ord-a04743cf1af7449c9f7919b0a3ceaa67
Source dataset
uspto-grants-2012_04
Patent number
US08153650B2

Reaction notes

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