Sodium Carbonate → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(1H-indazol-6-yl)-1-(1-methylethyl)-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 from 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), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (59.4 mg, 0.243 mmol), DMSO (1.5 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 55 mg (65%). LCMS E-S (M+H)=456.0 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49-1.65 (m, J=6.4 Hz, 6H), 2.14 (s, 3H), 2.23 (s, 3H), 4.43 (d, J=4.6 Hz, 2H), 5.36 (quin, J=6.7 Hz, 1H), 5.87-5.97 (m, 1H), 7.52-7.72 (m, 2H) 7.92 (d, J=8.6 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 8.16 (s, 1H), 8.26 (s, 1H), 8.37-8.49 (m, 2H), 8.96-9.14 (m, 1H), 11.59 (br. s., 1H).

Provenance & Evidence