5-Methyl-2H-pyrazolo[3,4-b]pyridine → HCID 71280284, compound

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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 (136 mg, 318 μmol), 5-methyl-1H-pyrazolo[3,4-b]pyridine (42.4 mg, 318 μmol) in dioxane (3.5 mL) was added sodium tert-butoxide (67.3 mg, 700 μmol) and bis(tri-tert-butylphosphine)palladium(0) (16.3 mg, 31.8 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-(5-methyl-1H-pyrazolo[3,4-b]pyridin-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide. 1H NMR (CDCl3) δ: 9.19 (s, 1H), 8.51 (d, J=1.8 Hz, 1H), 8.38 (s, 1H), 8.33 (s, 1H), 8.22 (s, 1H), 7.96 (dd, J=2.0, 1.0 Hz, 1H), 5.72 (s, 2H), 3.52-3.59 (m, 2H), 2.54 (s, 3H), 1.60 (s, 9H), 0.88-0.97 (m, 3H), −0.04 (s, 9H).

Provenance & Evidence