N,N'-Dimethylethylenediamine → N-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-N-methyl-benzamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 1-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.25 g, 0.61 mmol), N-Methyl-benzamide (0.243 g, 1.8 mmol), K2CO3 (0.185 g, 1.34 mmol), CuI (0.0175 g, 0.092 mmol) and N,N′-Dimethyl-ethane-1,2-diamine (0.02 mL, 0.184 mmol) in tolene was heated under an argon atmosphere in a microwave oven at 110° C. overnight. After cooling to room temperature, the reaction mixture was purified by flash column chromatography on silica gel with EtOAc in hexane (10% to 40% gradient over 30 min) to give the desired product (60 mg, 21% yield) as a yellow oil. 1H NMR (CDCl3, 300 MHz): δ 8.43 (s, 1H), 8.04 (s, 1H), 7.45-7.24 (m, 5H), 5.65 (s, 2H), 3.74 (s, 3H), 3.62-3.59 (m, 2H), 1.51 (s, 9H), 0.99-0.94 (m, 2H), 0 (s, 9H); MS [M+H]+: 467. Step 2: The general procedures as described in these Examples were followed. 1H NMR (CDCl3): δ 9.50 (s, 1H), 8.35 (s, 1H), 8.00 (s, 1H), 7.39-7.21 (m, 5H), 3.69 (s, 3H), 1.45 (s, 9H); MS [M+H]+: 337.

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