6-fluoro-1-methyl-3-(tributylstannyl)-1H-indazole → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (80 mg, 0.187 mmol) and 6-fluoro-1-methyl-3-(tributylstannyl)-1H-indazole (0.1 g, 0.228 mmol) were dissolved in DMF (3 mL). The reaction mixture was evacuated and filled with nitrogen. Copper(I) iodide (6.71 mg, 0.0749 mmol) and tetrakis(triphenylphosphine)palladium (0) (10.8 mg, 0.00936 mmol) were added. The reaction mixture was heated at 90° C. for 2 h. The mixture was cooled and partitioned between ethyl acetate and water, the organic phase washed with brine, then dried over magnesium sulfate. The crude compound was purified by chromatography using 25% ethyl acetate/hexanes to obtain 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (5 mg, 38%).

Provenance & Evidence