Bromine → 3-Bromo-6-iodoimidazo[1,2-A]pyridine

HRID 383307Notes

Reaction equation

HRID 383307 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[Br:11]Br>C(O)(=O)C>[Br:11][C:8]1[N:6]2[CH:7]=[C:2]([I:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27643276-Iodoimidazo(1,2-a)pyridine

Product 1

HCID 684848303-Bromo-6-iodoimidazo[1,2-A]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture comprising 6-iodo-imidazo[1,2-a]pyridine (1 eq, 95 mmol, 23.3 g) in acetic acid (220 ml) under an inert atmosphere of argon is added dropwise bromine (1 eq, 95 mmol, 4.8 ml). After stirring at room temperature for 1 hour, the reaction mixture is filtered. The resulting solid is suspended in DCM (1% MeOH) (500 ml) and washed with 4N sodium hydroxide (100 ml). When the solid dissolves, the organic layer is separated, dried (MgSO4) and evaporated to give a beige solid; [M+H]+323 (325).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washwashed with 4N sodium hydroxide (100 ml)
  3. dissolutionWhen the solid dissolves
  4. customthe organic layer is separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a beige solid

Sources & evidence

ORD record
ord-b16d9910126441a4bc47f93ceb23d1eb
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

Loading…