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

HRID 2173727Notes

Reaction equation

HRID 2173727 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 1) (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) was 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-050f49e1e44746e89208b7136c99d9ca
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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