Water → Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylate

HRID 908219Notes

Reaction equation

HRID 908219 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:18]=[C:19]([C:24]([Br:27])=[CH:25][N:26]=1)[C:20]([O:22][CH3:23])=[O:21].O>CO>[CH3:23][O:22][C:20]([C:19]1[C:24]([Br:27])=[CH:25][N:26]2[CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:16]=[C:17]2[CH:18]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

Product 1

HCID 67041599Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromoacetophenone (17.29 g, 87 mmol) and NaHCO3 (8.03 g, 96 mmol) were added to a solution of methyl 2-amino-5-bromoisonicotinate (20.07 g, 87 mmol) in methanol (240 ml), and the mixture was heated to reflux (5 h). After cooling to r.t., water (75 ml) was added, and the brown suspension was stirred (15 min) and filtered. The precipitate was washed with a small amount of methanol. The title compound (10.11 g, 35%) was dried under vacuum and was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (5 h)
  3. filtrationfiltered
  4. washThe precipitate was washed with a small amount of methanol
  5. dry with materialThe title compound (10.11 g, 35%) was dried under vacuum
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-d3b91ad9ce8b47729249315fd3d39a4b
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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