6-Methoxy-1H-indazole → N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

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To a stirred solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (200 mg, 468 μmol), 6-methoxy-1H-indazole (69.3 mg, 468 μmol) in dioxane (3.5 mL) was added sodium tert-butoxide (98.9 mg, 1.03 mmol) and bis(tri-tert-butylphosphine)palladium(0) (23.9 mg, 46.8 μmol). The mixture was degassed then heated in sealed tube at 125° C. for two days. The mixture was cooled, filtered through celite, the cake washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-30% ethyl acetate in hexanes) gave N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (131 mg, 57%). 1H NMR (CDCl3) δ: 9.06 (s, 1H), 8.33 (s, 1H), 8.18 (d, J=0.8 Hz, 1H), 7.95 (d, J=2.0 Hz, 1H), 7.80 (s, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.01 (dd, J=8.8, 2.3 Hz, 1H), 5.71 (s, 2H), 3.94 (s, 3H), 3.53-3.63 (m, 2H), 1.57 (s, 9H), 0.91-0.98 (m, 2H), −0.03 (s, 9H).

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