Sodium Carbonate → 5-Bromo-3-(4-fluorophenyl)pyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.058 g of 3,5-dibromo-pyrazin-2-ylamine in 100.0 ml 1,2-dimethoxyethane was added at room temperature 1.156 g of tetrakis(triphenylphosphine) palladium (0) and stirred for 0.5 hours. To the resulting mixture was added a solution of 5.30 g sodium carbonate in 50.0 ml water and 3.078 g 4-fluorophenylboronic acid. The mixture was heated to 100° C. for 5 h. The resulting yellow solution was partitioned between 10% aqueous citric acid and ethyl acetate. The organic layer washed with 10% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane to dichloromethane to yield 3.22 g of the title compound as white crystals. MS (ISP) (M+H+)=268.1 and 270.1

Provenance & Evidence