2-Amino-4-methylpyridine → 2-(4-Bromophenyl)-7-methylimidazo[1,2-a]pyridine

HRID 8376

Reaction equation

HRID 8376 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1>C(O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:12]=[C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]3[CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 74544-Bromophenacyl bromide

Product 1

HCID 7176442-(4-Bromophenyl)-7-methylimidazo[1,2-a]pyridineYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4′-dibromoacetophenone (22.4 g) and 2-amino-4-picoline (8.68 g) in ethanol (80 mL) was heated at reflux temperature for 3 hours. The reaction mixture was cooled to ambient temperature and the crystalline solid isolated by filtration, washed with ethanol and dried in vacuo to give the title compound (13.1 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. customthe crystalline solid isolated by filtration
  4. washwashed with ethanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e6db157d18cf461c8d370ac086ebe049
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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