Sodium Carbonate → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 74 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 1-methyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (73.8 mg, 0.243 mmol), DMSO(2 mL), sodium carbonate (0.281 mL, 0.562 mmol), and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 12 mg (13%). LCMS E-S (M+H)=515.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (d, J=6.4 Hz, 6 H), 2.13 (s, 3 H), 2.23 (m, 6 H), 2.37-2.46 (m, 4 H), 3.56-3.69 (m, 4 H), 4.40 (d, J=4.6 Hz, 2 H), 5.30 (quin, J=6.7 Hz, 1 H), 5.91 (s, 1 H), 6.99 (d, J=9.1 Hz, 1 H), 8.10 (s, 1 H), 8.32 (s, 1 H), 8.38 (dd, J=9.1, 2.5 Hz, 1 H), 8.91 (br. s., 1 H), 9.03 (d, J=2.3 Hz, 1 H).

Provenance & Evidence