Sodium t-butoxide → HCID 71280013, 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 (150 mg, 351 μmol) and 5,6-difluoro-1H-indazole (54.1 mg, 351 μmol) in dioxane (5.25 mL) was added sodium tert-butoxide (74.2 mg, 772 μmol) and bis(tri-tert-butylphosphine)palladium(0) (17.9 mg, 35.1 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-(5,6-difluoro-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (120 mg, 68%). 1H NMR (CDCl3) δ: 9.17 (s, 1H), 8.50 (d, J=2.5 Hz, 1H), 8.44 (dd, J=10.0, 6.8 Hz, 1H), 8.37 (s, 1H), 8.30 (s, 1H), 8.24 (d, J=0.8 Hz, 1H), 5.72 (s, 2H), 3.55-3.61 (m, 2H), 1.61 (s, 9H), 0.93-0.96 (m, 2H), −0.03 (s, 9H).

Provenance & Evidence