Sodium Iodide → 5-Iodo-3-(trifluoromethyl)pyridin-2-amine

HRID 1293638Notes

Reaction equation

HRID 1293638 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[I-:13].[Na+]>C(O)CCC.[Cu]I.CNCCNC>[I:13][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 5238Sodium IodideHCID 205253835-Bromo-3-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 582353065-Iodo-3-(trifluoromethyl)pyridin-2-amineYield 102%

Reagents, catalysts & solvents 3

HCID 8070N,N'-DimethylethylenediamineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 5-bromo-3-trifluoromethyl-pyridin-2-ylamine (example C.18 step 3) (723 mg, 3 mmol), sodium iodide (900 mg, 6 mmol), copper (I) iodide (29 mg, 5 mol %) and N,N′-dimethylethylendiamine (26 mg, 10 mol %) in n-butanol (6 mL) was stirred at reflux under argon atmosphere for 18 h. The reaction mixture was cooled to 23° C., extracted with ethyl acetate and water, the organic layers were dried over MgSO4, filtered and evaporated to leave the title compound as a brown solid (880 mg, 102%), which was used without further purification. MS (ISN) 287.0 [(M−H)−].

Workup

  1. temperatureat reflux under argon atmosphere for 18 h
  2. extractionextracted with ethyl acetate and water
  3. dry with materialthe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-aac3639ccbb341849dff29a2b410006a
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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