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

HRID 444925Notes

Reaction equation

HRID 444925 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-57bbf8d64c19419682090e593262ed0c
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

Loading…