Potassium Carbonate → N-tert-butyl-2-(1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (50 mg, 117 μmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (37.0 mg, 152 μmol), potassium carbonate (16.2 mg, 117 μmol) were combined in a reaction tube with a teflon-threaded seal, dioxane (2.5 mL) and water (0.5 mL) were added, then the mixture degassed with nitrogen for 1 min. Tetrakis(triphenylphosphine)palladium(0) (13.5 mg, 11.7 μmol) was added, nitrogen was bubbled through for 1 minute, then the reaction was heated to 85° C. for 6 h, and then at 75° C. for an additional 15 h. The reaction mixture was cooled, concentrated in vacuo, and the residue purified by chromatography (silica, 1-15% ethyl acetate in hexanes) to give N-tert-butyl-2-(1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (54 mg) as an oil which slowly crystallized. MS (M+H)+=464.2.

Provenance & Evidence