2-Chloropyridin-4-amine → 2-Chloro-5-iodopyridin-4-amine

HRID 1619121Notes

Reaction equation

HRID 1619121 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=1>CN(C=O)C>[Cl:9][C:10]1[CH:15]=[C:14]([NH2:16])[C:13]([I:1])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 844322-Chloropyridin-4-amineHCID 120273N-Iodosuccinimide2×

Product 1

HCID 454803662-Chloro-5-iodopyridin-4-amineYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-iodosuccinimide (15.75 g, 70 mmol) was added to a solution of 2-chloropyridin-4-amine (9.00 g, 70 mmol) in N,N′-dimethylformamide (140 mL) and the mixture was stirred at 80° C. for 6 hours. Further N-iodosuccinimide (7.80 g, 35 mmol) was added and the mixture was stirred at 60° C. overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium thiosulphate, water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (6:1 to 2:1 hexanes/ethyl acetate) to yield the title compound (6.80 g, 38%) as a beige solid.

Workup

  1. stirringthe mixture was stirred at 60° C. overnight
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium thiosulphate, water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (6:1 to 2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8b547f98ca9e4f16b37a24db10ff5949
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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