N,N'-Dimethylethylenediamine → 2-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydro-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

Toluene was added to a mixture of 1-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.250 g, 0.606 mmol), 2,3-Dihydro-isoindol-1-one (0.097 g, 0.727 mmol), copper iodide (11.6 mg, 0.061 mmol), and potassium carbonate (0.168 g, 1.212 mmol) under argon. Dimethyl ethylenediamine (0.013 mL; 0.011 g, 0.121 mmol) was subsequently added and the reaction was stirred for 16 h at 110° C. The reaction was diluted with ethyl acetate and filtered through a silica plug before being concentrated in vacuo. Silica gel chromatography (0->25% EtOAc/hexanes over 30 minutes) afforded 0.2206 g (78% yield) of 2-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydro-isoindol-1-one. MS (E/I): 465 (M+H)

Provenance & Evidence