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

HRID 1747841Notes

Reaction equation

HRID 1747841 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 (II) 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 (II) was collected by filtration as a brown solid in 90% yield

Sources & evidence

ORD record
ord-b44c20aa515948ec94b7863e73d4a1e6
Source dataset
uspto-grants-2015_10
Patent number
US09150594B2

Reaction notes

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