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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 328 μmol), 6-fluoro-1H-indazole (43.0 mg, 316 mmol) in dioxane (2 mL) was added sodium tert-butoxide (66.8 mg, 695 μmol) and bis(tri-tert-butylphosphine)palladium(0) (16.1 mg, 31.6 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, 0-40% ethyl acetate in hexanes) gave N-tert-Butyl-2-(6-fluoro-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide. 1H NMR (CDCl3) δ: 9.17 (s, 1H), 8.36 (s, 1H), 8.29 (dd, J=9.3, 2.3 Hz, 1H), 8.26 (d, J=1.0 Hz, 1H), 7.80 (dd, J=8.8, 5.0 Hz, 1H), 7.66 (s, 1H), 7.12 (td, J=8.9, 2.3 Hz, 1H), 5.72 (s, 2H), 3.54-3.63 (m, 2H), 1.62 (s, 9H), 0.90-1.00 (m, 2H), −0.03 (s, 9H).

Provenance & Evidence