N-bromobutanimide → 3-bromo-5H,6H,7H,8H-imidazo[1,2-a]pyridine

HRID 2238643Notes

Reaction equation

HRID 2238643 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:10][C:3]1[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 99892645H,6H,7H,8H-imidazo[1,2-a]pyridine

Product 1

HCID 100356983-bromo-5H,6H,7H,8H-imidazo[1,2-a]pyridineYield 25.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

375 mg of the 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [44-1] was dissolved in 10 mL of carbon tetrachloride, then 546 mg of N-bromosuccinimide was added, and the mixture was heated for 30 minutes under reflux. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography and then by preparative thin-layer chromatography sequentially, to obtain 155 mg of 3-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [44-2] as a pale yellow solid.

Workup

  1. temperaturethe mixture was heated for 30 minutes
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7fb63aabd4374955aa2831c51f16155d
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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