6-Methyl-1H-indazole → HCID 71279530, compound

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-methyl-1H-indazole (41.7 mg, 316 μmol) 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 15 h. 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-methyl-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide. 1H NMR (CDCl3) d: 9.08 (s, 1H), 8.35 (s, 1H), 8.30 (s, 1H), 8.23 (d, J=1.0 Hz, 1H), 8.03 (br. s., 1H), 7.85 (s, 1H), 7.29 (s, 1H), 5.72 (s, 2H), 3.55-3.61 (m, 2H), 2.50 (s, 3H), 1.59 (s, 9H), 0.77-1.01 (m, 2H), −0.03 (s, 9H).

Provenance & Evidence