2-Bromo-4'-methylacetophenone → Methyl 2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylate

HRID 1185991Notes

Reaction equation

HRID 1185991 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][N:14]=1>C(O)C>[C:8]1([CH3:11])[CH:9]=[CH:10][C:5]([C:3]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][N:14]3[CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 737487Methyl 6-aminonicotinate

Product 1

HCID 16088231Methyl 2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylateYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-4′-methylacetophenone 2 (14.5 g, 65.1 mmol) was added to a hot solution of methyl 2-aminopyridine-5-carboxylate 1 (9.0 g, 61.1 mmol) in ethanol (280 ml). The solution was then heated at reflux for 6 h, cooled to room temperature and the white solid filtered and washed with ethanol to give methyl 2-(4-tolyl)-imidazo[1,2-a]pyridine-6-carboxylate 3 (13.9 g, 80%).

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 6 h
  3. filtrationthe white solid filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-07e84fe958d141a1bd7ef71b27958dfa
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

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