Ethyl bromopyruvate → Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate

HRID 467823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467823
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>COCCOC>[Br:8][C:7]1[C:2]2[N:3]([CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:1]=2)[CH:4]=[C:5]([C:9]([F:12])([F:10])[F:11])[CH:6]=1

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amine

Produkt 1

HCID 86664721Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylateAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-3-bromo-5-(trifluoromethyl)pyridine (10.0 g, 41.5 mmol) in 1,2 dimethoxyethane (300 mL) at room temperature was added ethyl bromopyruvate (9.889 g, 45.64 mmol) dropwise. The reaction mixture was heated to reflux for 18 h. The 1,2-dimethoxyethane was removed under reduced pressure and the residual solid was recrystallized from 1-chlorobutane. The solid was isolated by filtration and dried to afford an off-white solid, 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid, ethyl ester (11.044 g).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe 1,2-dimethoxyethane was removed under reduced pressure
  4. customthe residual solid was recrystallized from 1-chlorobutane
  5. customThe solid was isolated by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0b7f42c6d6d5439da1e9827d5f87c50a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623890B2

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