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

HRID 1824509Notes

Reaction equation

HRID 1824509 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-5bb051e282244be59cd34ecde14aabce
Source dataset
uspto-grants-2006_05
Patent number
US07041827B2

Reaction notes

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