6-chloro-1-methyl-3-tributylstannanyl-1H-indazole → tert-butyl 3-(2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)cyclohexylcarbamate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 6-chloro-1-methyl-3-(tributylstannyl)-1H-indazole (0.47 g, 1.03 mmol), tert-butyl 3-(2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)cyclohexylcarbamate (0.45 g, 1.03 mmol), CuI (0.07 g, 0.37 mmol) and Pd(PPh3)4 (0.07 g, 0.06 mmol) in 100 mL of DMF was stirred at 80° C. under nitrogen atmosphere overnight. The solvent was removed under reduced pressure and the residue was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 50% acetonitrile/50% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 85% acetonitrile/15% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give tert-butyl 3-(2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)cyclohexylcarbamate (0.3 g, 56%) as a yellow solid. MS: (M+H)+=542.2; 1H NMR (300 MHz, DMSO): δ 9.13-9.07 (m, 1H), 8.48-8.39 (m, 2H), 8.13-8.01 (m, 2H), 7.42-7.30 (m, 1H), 5.20 (s, 3H), 3.44-3.35 (m, 1H), 2.30-2.05 (m, 1H), 1.82-1.38 (m, 4H), 1.32-1.17 (m, 13H).

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