Water → 6-Bromo-3-iodoimidazo(1,2-a)pyridine

HRID 1792428Notes

Reaction equation

HRID 1792428 reaction equation
[I:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:16]=[CH:17][N:18]=2)[CH:15]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].O>CN(C)C=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([I:1])=[CH:17][N:18]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 27955476-Bromoimidazo[1,2-a]pyridine

Product 1

HCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridineYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.7 g N-iodosuccinimide was added in divided portions to 100 mL solution of 9 g 6-bromoimidazo[1,2-a]pyridine in N,N-dimethylformamide, and the mixture was stirred for 2 hours. An aqueous sodium thiosulfate solution was added thereto and stirred for 1 hour, water was added thereto, and the formed crystals were collected by filtration. The product was recrystallized from tetrahydrofuran/ethanol to give 13.5 g of the title compound (colorless crystals).

Workup

  1. stirringstirred for 1 hour
  2. filtrationthe formed crystals were collected by filtration
  3. customThe product was recrystallized from tetrahydrofuran/ethanol

Sources & evidence

ORD record
ord-91676370c4b44065a709dbf40d068486
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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