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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.1 g, 0.337 mmol), isoquinolin-8-ylboronic acid (64 mg, 0.37 mmol), Pd2 dba3 (77 mg, 0.067 mmol), X-Phos (64 mg, 0.135 mmol) and Na2CO3 (107 mg, 1.01 mmol) in dioxane (20 mL) and water (5 mL) was heated to 90° C. for 16 hours under N2 atmosphere. Reaction mixture was concentrated and the residue was purified by preparative-TLC (methanol:dichloromethane=1:10) to afford N-tert-butyl-2-(isoquinolin-8-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (76 mg, 66%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 11.77 (s, 1H), 9.95 (s, 1H), 8.89 (s, 1H), 8.69 (d, 1H, J=5.7 Hz), 8.45 (s, 1H), 8.41 (s, 1H), 8.01-7.84 (m, 4H), 1.46 (s, 9H). LCMS: (M+H)+=346.

Provenance & Evidence