Imidazole → 2-Bromo-5-(1H-imidazol-1-YL)pyrazine

HRID 1157313Notes

Reaction equation

HRID 1157313 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Br:8][C:9]1[C:14](Br)=[N:13][CH:12]=[CH:11][N:10]=1>C1COCC1>[Br:8][C:9]1[CH:14]=[N:13][C:12]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 138675722,3-Dibromopyrazine

Product 1

HCID 457877272-Bromo-5-(1H-imidazol-1-YL)pyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To sodium hydride (0.20 g) in THF (15 ml), imidazole (0.57 g) was added and cooled to 0° C. To the above mixture 2,3-dibromopyrazine (2 g) was added and entire reaction mixture was allowed to reflux for overnight. The reaction mixture was quenched with water 5 ml volatiles were removed under vacuum. The resulting crude mass was purified by column chromatography to afford 2-bromo-5-(1H-imidazol-1-yl)pyrazine as pure product.

Workup

  1. temperatureto reflux for overnight
  2. customThe reaction mixture was quenched with water 5 ml volatiles
  3. customwere removed under vacuum
  4. customThe resulting crude mass was purified by column chromatography

Sources & evidence

ORD record
ord-f69f9197ee764a688b680a162427364b
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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