Trifluoroacetic acid → 2-Amino-5-bromo-3-iodopyridine

HRID 1625013Notes

Reaction equation

HRID 1625013 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[I:16]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]([I:16])=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 706222-Amino-5-bromopyridineHCID 120273N-Iodosuccinimide

Product 1

HCID 15165082-Amino-5-bromo-3-iodopyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-amino-5-bromopyridine (2) in DMF was added trifluoroacetic acid (1.2 equiv). At room temperature, N-iodosuccinimide (1.1 equiv) was added and the reaction mixture was heated at 50° C. for 3 h. HPLC indicated complete conversion. After cooling to room temperature the product was precipitated by adding the reaction mixture to water. After neutralization with sodiumthiosulfate and 1N NaOH the title compound (11) was collected by filtration as a brown solid in 90% yield.

Workup

  1. temperatureAfter cooling to room temperature the product
  2. customwas precipitated
  3. additionby adding the reaction mixture to water
  4. filtrationAfter neutralization with sodiumthiosulfate and 1N NaOH the title compound (11) was collected by filtration as a brown solid in 90% yield

Sources & evidence

ORD record
ord-b101bece693f4b58a9c023edc62c1e54
Source dataset
uspto-grants-2014_07
Patent number
US08779150B2

Reaction notes

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