N,N'-Dimethylethylenediamine → HCID 58438637, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (700 mg, 1.96 mmol), 4-chloro-2,3-dihydro-isoindol-1-one (395 mg, 2.36 mmol), N,N′-dimethylethylenediamine (42 μL, 0.39 mmol) and potassium carbonate (543 mg, 3.93 mmol) under argon atmosphere. Copper(I) iodide (37 mg, 0.20 mmol) was added and the reaction mixture was heated at 100° C. for 24 h. The reaction mixture was allowed to reach room temperature and then diluted with EtOAc (50 mL). The slurry was filtered over a celite pad and the filtrate was evaporated under vacuum. The crude residue was purified by column chromatography (SiO2, 100 g, EtOAc:hexanes, 0-70% in 30 min) to provide 170 mg (20%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as an off-white solid and 400 mg of recovered starting material.

Provenance & Evidence