N-bromobutanimide → 3-Bromo-8-phenylimidazo[1,2-a]pyridine

HRID 1982538Notes

Reaction equation

HRID 1982538 reaction equation
[C:1]1([C:7]2[C:8]3[N:9]([CH:13]=[CH:14][N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)Cl>[Br:16][C:13]1[N:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]2=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 137640278-Phenylimidazo[1,2-a]pyridine

Product 1

HCID 233169583-Bromo-8-phenylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 2 g (10.3 mmol) of the product from Example 4 with 1.8 g (10.3 mmol) of N-bromosuccinimide in 50 ml of methylene chloride, and stir for 10 minutes at room temperature. Wash the reaction mixture with 50 ml of 10% potassium carbonate. Dry the methylene chloride layer over sodium sulfate, treat with charcoal, filter, and remove the solvent in vacuo. Crystallize the residue from ether to provide the title compound.

Workup

  1. washWash the reaction mixture with 50 ml of 10% potassium carbonate
  2. dry with materialDry the methylene chloride layer over sodium sulfate
  3. additiontreat with charcoal
  4. filtrationfilter
  5. customremove the solvent in vacuo
  6. customCrystallize the residue from ether

Sources & evidence

ORD record
ord-72484a54a434498d87ac3b9620ad69f4
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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