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

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Reaction Steps

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.

Provenance & Evidence