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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (320 mg, 749 μmol) and 7-ethyl-3-iodo-1H-indazole (244 mg, 898 μmol) in DMF (2.5 mL) was added 1,1,1,2,2,2-hexabutyldistannane (651 mg, 412 μL, 1.12 mmol) under N2. After 10 min tetrakis(triphenylphosphine)palladium (0) (43.3 mg, 37.4 mmol) was added and the reaction mixture heated to 115° C. After 16 h the reaction was cooled and concentrated. The residue was diluted with 10% methanol/dichloromethane and filtered through a pad of celite. Purification of the filtrate by chromatography (silica, 5-45% ethyl acetate/hexane) gave N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (45 mg, 91.3 μmol, 12%) as an off-white solid. MS (M+H)+=493.4; 1H NMR (CDCl3) δ: 10.57 (s, 1H), 9.34 (s, 1H), 8.49 (d, J=7.5, 1H), 8.43 (s, 1H), 8.24 (s, 1H), 7.35 (d, J=7.1 Hz, 1H), 7.29 (t, J=7.1 Hz, 1H), 5.77 (s, 2H), 3.62 (t, J=8.3, 2H), 3.07 (q, J=7.5 Hz, 2H), 1.68 (s, 9H), 1.50 (t, J=7.5 Hz, 3H), 0.98 (t, J=8.3, 2H), 0.0 (s, 9H).

Provenance & Evidence