1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole → N-tert-butyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (100 mg, 234 μmol) and 1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole (99.5 mg, 234 μmol) were dissolved in DMF (2.5 mL) under argon, tetrakis(triphenylphosphine)palladium (0) (13.5 mg, 11.7 μmol) and CuI (8.91 mg, 46.8 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 (60 g column, 50 μm from Analogix, 0-50% EtOAc in hexanes over 30 min) to give N-tert-butyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (25 mg, 51.8 μmol, 22.1%) as an off-white solid. MS (M+Na)+=505; 1H NMR (CDCl3) δ: 9.12 (s, 1H), 8.33 (s, 1H), 8.02 (s, 1H), 5.73 (s, 2H), 3.90 (s, 3H), 3.54-3.68 (m, 2H), 3.06 (t, J=6.0 Hz, 2H), 2.63-2.78 (m, 2H), 1.91-2.06 (m, 2H), 1.77-1.90 (m, 2H), 1.62 (s, 9H), 0.95-1.02 (m, 2H), 0.00 (s, 9H).

Provenance & Evidence