Hydrogen Bromide → 6-Bromo-8-iodoimidazo[1,2-a]pyridine

HRID 402945Notes

Reaction equation

HRID 402945 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH2:11][CH:12](OC)OC.Br>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]2[N:6]([CH:11]=[CH:12][N:8]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 15165082-Amino-5-bromo-3-iodopyridine

Product 1

HCID 712991706-Bromo-8-iodoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-bromo-3-iodopyridin-2-amine (1.0 g, 3.34 mmol) and 2-bromo-1,1-dimethoxyethane were dissolved in ethanol (20 ml). To this solution was added a 50% mixture of HBr in water (4 ml). The mixture was stirred at reflux temperature overnight. After the completion of the reaction, the mixture was cooled to room temperature and filtered. The residue was suspended in DCM (10 ml) and stirred with the saturated aqueous solution of Na2CO3. The organic layer was separated and washed with saturated brine, dried over sodium sulfate and concentrated. The desired product was obtained as a yellow solid (950 mg, yield 88%). LC-MS: 323 [M+1]+, tR=1.299 min.

Workup

  1. temperatureat reflux temperature overnight
  2. customAfter the completion of the reaction
  3. filtrationfiltered
  4. stirringstirred with the saturated aqueous solution of Na2CO3
  5. customThe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-86e5b1beb5d540a2900b38aa5704dcc6
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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