Ammonia → 5-Bromo-3-iodo-4-methylpyridin-2-amine

HRID 1625987Notes

Reaction equation

HRID 1625987 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[I:10]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.N>C(O)(=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([I:10])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 8176952-Amino-5-bromo-4-methylpyridine

Product 1

HCID 401518975-Bromo-3-iodo-4-methylpyridin-2-amineYield 94.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Bromo-4-methylpyridine-2-amine (3.1 g) was dissolved in acetic acid (20 ml). N-Iodosuccinimide (3.8 g) and trifluoroacetic acid (0.2 ml) were added and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was poured into ice water and neutralized with 28% aqueous ammonia. Then, the precipitated solid was collected by filtration, washed with water and dried to give the title compound (4.9 g).

Workup

  1. filtrationThen, the precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d0c314362db740fca60b7e1eab165bfd
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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