Sodium Carbonate → N-tert-butyl-2-(isoquinolin-8-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 2-bromo-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.5 g, 0.928 mmol), 1H-indazol-4-ylboronic acid (165 mg, 1.02 mmol), Pd(PPh3)4 (214 mg, 0.186 mmol), X-Phos (177 mg, 0.371 mmol) and Na2CO3 (295 mg, 2.78 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100° C. for 16 hours under N2 atmosphere. Reaction mixture was concentrated and the residue was purified by preparative-TLC (eluting with methanol:dichloromethane=1:100) to afford N-tert-butyl-2-(isoquinolin-8-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (375 mg, 70%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 10.37 (s, 1H), 8.61 (s, 1H), 8.60 (s, 1H), 8.54 (s, 1H), 8.36 (s, 1H), 7.55-7.49 (m, 3H), 7.30-7.26 (m, 9H), 7.22-7.18 (m, 6H), 1.53 (s, 9H). LCMS: (M+H)+=577.

Herkunft & Nachweise