2-bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide → 2-(5-(3-chlorophenoxy)-1-methyl-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (103 mg, 250 μmol) and 5-(3-chlorophenoxy)-1-methyl-3-(tributylstannyl)-1H-indazole (219 mg, 400 μmol.6) were dissolved in DMF (2.5 mL) under argon, tetrakis(triphenylphosphine)palladium (0) (14.4 mg, 12.5 μmol) and CuI (9.52 mg, 50.0 μmol, Eq: 0.20) were added and the mixture sonicated for 5 min with bubbling argon. The reaction mixture was stirred at 90° C. (oil bath temperature) for 2.5 h. The reaction mixture was concentrated under high vacuum and the residue was purified by chromatography (40 g column, 50 μm from Analogix, 0-50% over 30 min) to give 2-(5-(3-chlorophenoxy)-1-methyl-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (113 mg, 191 μmol, 77%) as a light yellow solid. 1H NMR (CDCl3) δ: 9.27 (s, 1H), 8.32 (s, 1H), 8.28 (d, J=2.3 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 7.17-7.28 (m, 2H), 6.97-7.06 (m, 1H), 6.79-6.90 (m, 2H), 5.71 (s, 2H), 4.28-4.46 (m, 1H), 4.23 (s, 3H), 3.51-3.66 (m, 2H), 1.22 (d, J=6.4 Hz, 6H), 0.85-1.03 (m, 2H), −0.04 (s, 9H).

Provenance & Evidence