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

HRID 1474172Notes

Reaction equation

HRID 1474172 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 86664721Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylateYield 78.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6a03ad3f088f4e9fb9a07b0efd2649e4
Source dataset
uspto-grants-2015_04
Patent number
US09018228B2

Reaction notes

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