CS(=O)(=O)c1ccc(N)cc1.Clc1cncc(Cl)n1>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1
2,6-dichloropyrazine (287 mg, 1.93 mmol), 4-(methylsulfonyl)aniline (330 mg, 1.93 mmol), diacetoxypalladium (43.3 mg, 0.19 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (120 mg, 0.19 mmol) and cesium carbonate (690 mg, 2.12 mmol) in 1,4-dioxane (2 mL) were degazed and stirred at 90 °C for 16 hours under nitrogen. The reaction mixture was evaporated to dryness and was purified by preparative HPLC using a Waters SunFire reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford 6-chloro-N-(4-(methylsulfonyl)phenyl)pyrazin-2-amine (120 mg, 21.95 %) as a yellow solid.
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