2-bromo-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide → N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

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In a round-bottomed flask, 2-bromo-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (530 mg, 1 mmol) and 5-(difluoromethoxy)-3-(tributylstannyl)-1H-indazole (470 mg, 1 mmol) were dissolved in DMF (10 mL) under nitrogen. Pd(PPh3)4 (58 mg, 0.05 mmol) and CuI (38 mg, 0.2 mmol) were added and mixture sonicated for 5 min while bubbling nitrogen. The reaction mixture was stirred at 80° C. for 4 hours. The concentrated mixture was purified by column chromatography on silica gel eluting with petroleum ether/EtOAc (3:1 to 1:1, v/v) to give N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (410 mg, 64%) as a solid. MS: (M+H)+=643.2; 1H NMR (300 MHz, CDCl3): δ 8.85 (d, 1H, J=2.4 Hz), 8.35 (s, 1H), 8.26 (s, 1H), 8.13 (s, 1H,), 7.52-7.48 (m, 1H), 6.51 (t, 1H, J=74.0 Hz), 1.60 (s, 9H).

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