Water → Ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylate

HRID 570178Notes

Reaction equation

HRID 570178 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>COCCOC>[CH2:18]([O:17][C:15]([C:14]1[N:1]=[C:2]2[CH:7]=[N:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][N:3]2[CH:13]=1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 66144Ethyl bromopyruvateHCID 133411155-(Trifluoromethyl)pyrazin-2-amine

Product 1

HCID 67516905Ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-5-(trifluoromethyl)pyrazine (500 mg, 3.07 mmol) in 1,2-dimethoxyethane (10 mL) was added dropwise ethyl bromopyruvate (0.5 mL, 4.0 mmol). The reaction mixture was warmed to 60° C. for 72 hours. The reaction mixture was then cooled to room temperature, and water was added (10 mL) to precipitate a solid. The suspension was stirred for 10 minutes, filtered, and the isolated solid was washed with water to afford the desired ester which was used in the next step without further drying. 1H NMR (CDCl3) δ 9.22 (s, 1H), 8.59 (s, 1H), 8.39 (s, 1H), 4.50 (q, 2H), 1.47 (t, 3H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customto precipitate a solid
  3. filtrationfiltered
  4. washthe isolated solid was washed with water

Sources & evidence

ORD record
ord-64538f5d37134e94bbfbf800a18ef048
Source dataset
uspto-grants-2015_05
Patent number
US09023850B2

Reaction notes

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