Bromine → 3-Bromo-6-chloroimidazo[1,2-a]pyridine

HRID 383309Notes

Reaction equation

HRID 383309 reaction equation
[Cl: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]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27643286-Chloroimidazo(1,2-a)pyridine

Product 1

HCID 457900423-Bromo-6-chloroimidazo[1,2-a]pyridineYield 109.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 6-chloro-imidazo[1,2-a]pyridine (1 eq, 253 mmol, 39 g) in acetic acid (500 ml) under inert atmosphere, is added dropwise bromine (1 eq, 253 mmol, 13 ml). After 1 hour stirring at room temperature, the reaction mixture is filtered and to give a beige solid (64 g) 3-Bromo-6-chloro-imidazo[1,2-a]pyridine hydrobromide; [M+H]+232 (234)

Workup

  1. filtrationthe reaction mixture is filtered

Sources & evidence

ORD record
ord-03eec8a302ca479eb68e62273cc9109a
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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