Iodine → 2-Amino-5-chloro-3-iodopyridine

HRID 925322Notes

Reaction equation

HRID 925322 reaction equation
[I:1]I.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:3][C:4]1[CH:5]=[C:6]([I:1])[C:7]([NH2:10])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 661742-Amino-5-chloropyridine

Product 1

HCID 110760102-Amino-5-chloro-3-iodopyridineYield 64%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

5-chloro-3-iodopyridin-2-amine was prepared according to method D Step I with Iodine (7.55 g; 29.73 mmol) was added to a mixture of 5-chloropyridin-2-amine (3.00 g; 22.87 mmol) and silver sulphate (9.36 g; 29.73 mmol) in ethanol (150 mL). The crude residue was purified by flash chromatography on silica gel (eluent 0 to 30% of ethyl acetate in heptane) to give 3.71 g (64%) of 5-chloro-3-iodopyridin-2-amine as a beige solid.

Workup

  1. custom5-chloro-3-iodopyridin-2-amine was prepared
  2. customThe crude residue was purified by flash chromatography on silica gel (eluent 0 to 30% of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a3c73dc43afe481d9d40d2ece8629aa0
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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