Sodium hydride (180 mg, 4.50 mmol) was added to a suspension of indazole (543 mg, 4.40 mmol) in N,N-dimethylformamide (5 mL) and the reaction mixture was stirred at 50° C. for 20 minutes. To this suspension N-(4-chloro-phenyl)-N-(6-chloro-pyrazin-2-yl)-2,2-dimethyl-propionamide (300 mg, 0.88 mmol) was added and stirred at 100° C. over night. The reaction mixture was quenched with brine and extracted with ethyl acetate (4×15 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and evaporated. The crude product was purified by column chromatography with ethyl acetate-heptane as eluent to give (4-chloro-phenyl)-(6-indazol-2-yl-pyrazin-2-yl)-amine (17 mg, 13%, Mp 249-252° C., LC-ESI-HRMS of [M+H]+ shows 322.0864 Da. Calc. 322.085948 Da, dev. 1.4 ppm) as a yellow solid, and (4-chloro-phenyl)-(6-indazol-1-yl-pyrazin-2-yl)-amine (19 mg, 12%, Mp. 204-207° C., LC-ESI-HRMS of [M+H]+ shows 322.0876 Da. Calc. 322.085948 Da, dev. 5.1 ppm) as a brown solid.
