Isoamyl Nitrite → 5-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

HRID 1865875Notes

Reaction equation

HRID 1865875 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](N)=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:6]=1)=[O:4].N(OCCC(C)C)=O.C[Si](C)(C)[Br:29].C(=O)(O)[O-].[Na+]>BrCBr>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([Br:29])=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 675046415-Amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 866169575-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent2×

Procedure

To a suspension of 1.26 g 5-amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester in 25.0 ml dibromomethane was added 0.85 ml isoamyl nitrite. To the resulting suspension was added during 30 minutes a solution of 0.82 ml trimethyl bromosilane in 5 ml dibromomethane at room temperature. The mixture was stirred at room temperature for 2 hours. To the resulting turbid solution was added 10% aqueous sodium bicarbonate, the phases were separated and the organic layer was dried over magnesium sulfate, evaporated and purified by chromatography on silica gel using a gradient of heptane to 10% ethyl acetate in heptane to yield 0.81 g of the title compound as white crystals. MS (ISP) (M+H+)=311.1 and 313.0.

Workup

  1. customthe phases were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. custompurified by chromatography on silica gel using a gradient of heptane to 10% ethyl acetate in heptane

Sources & evidence

ORD record
ord-ec431b29cd344db9a467ee56972b406f
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

Loading…