2-Aminopyridine → 2-(2-Bromophenyl)imidazo[1,2-a]pyridine

HRID 1199472

Reaction equation

HRID 1199472 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Br:18])=O>C(O)C>[Br:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 27375222-Bromophenacyl Bromide

Product 1

HCID 28623882-(2-Bromophenyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-aminopyridine (1.63 g) and 2-bromo-1-(2-bromophenyl)-ethanone (4.8 g) in dry ethanol (40 mls) was heated under reflux for 1 hour. The mixture was concentrated in vacuo. The residue was treated with dilute sodium bicarbonate solution and extracted with ethyl acetate. The ethyl acetate was washed with water and brine then dried and evaporated. Flash chromatography produced the sub-title compound as a light grey oil. MS MW 272/274 bp 272.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. additionThe residue was treated with dilute sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate was washed with water and brine
  6. customthen dried
  7. customevaporated

Sources & evidence

ORD record
ord-5dac21755698435cbc12774be3fba360
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Linked notes

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