3-Chloro-4-fluoroaniline → 2-(3-Chloro-4-fluorophenylamino)-6-(3-acetamidophenyl)-pyrazine

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Using Method K. 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 3-chloro-4-fluoroaniline (42 mg, 0.29 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 80° C. for 12 hours. The same workup as for Method K and a combination of column chromatography and preparative TLC furnished 4 mg of title compound. Yield: 4.7%. 1H NMR (250 MHz, DMSO-d6) δ 2.09 (s, 3 H), 7.38 (d, 1 H, J=9.5 Hz), 7.46 (d, 1 H. J=7.9 Hz), 7.61 (d, 1 H, J=7.9 Hz), 7.72 (d, 1 H, 7.5 Hz), 7.86-7.91 (m, 1 H), 8.00-8-04 (m, 1H), 8.18 (s, 1 H), 8.40 (bs, 1 H), 8.48 (s, 1 H), 9.80 (s, 1 H), 10.08 (s, 1 H); m/z 357.2 [(M+H)+, calcd for C18H14ClFN4O 356.1].

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