Sodium Carbonate → Ethyl 3-amino-6-bromo-5-(trifluoromethyl)pyrazine-2-carboxylate

HRID 887858Notes

Reaction equation

HRID 887858 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Br:23]Br>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([C:13]([F:15])([F:16])[F:14])=[C:8]([Br:23])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 24408Bromine2×HCID 58442356HCID 58442356, compound2×

Product 1

HCID 72942096Ethyl 3-amino-6-bromo-5-(trifluoromethyl)pyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 962WaterSolvent

Procedure

To a solution of 3-amino-5-trifluoromethyl-pyrazine-2-carboxylic acid ethyl ester (Intermediate B) (30 mg, 0.13 mmol) in acetic acid (5 ml), sodium carbonate (15 mg, 0.14 mmol) was added. To this mixture, half the contents of a solution of bromine (7 μL, 0.13 mmol) in acetic acid (5 ml) were added, followed by the addition of sodium carbonate ((15 mg, 0.14 mmol). The remaining solution of bromine in acetic acid was added and the reaction mixture was left to stir at RT for 2 hours. The mixture was diluted with water and the resulting yellow precipitate was filtered under vacuum to afford the title compound.

Workup

  1. waitthe reaction mixture was left
  2. filtrationthe resulting yellow precipitate was filtered under vacuum

Sources & evidence

ORD record
ord-0740ecf025474d77877812a299f8ba39
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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