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

HRID 908219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908219
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d3b91ad9ce8b47729249315fd3d39a4b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017604B2

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