Sodium Carbonate → 6-(2,1,3-Benzoxadiazol-5-yl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-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 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.180 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzoxadiazole (57.7 mg, 0.235 mmol), DMSO (2 mL), sodium carbonate (0.271 mL, 0.541 mmol), and bis(triphenylphosphine)palladium(II) chloride (12.67 mg, 0.018 mmol) wherein the reaction time was 8 h. The final product was collected as 17 mg (20%). LCMS LCMS E-S (M+H)=472.4 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (d, J=6.8 Hz, 6H), 2.12 (s, 3H), 2.27 (s, 3H) 4.42 (d, J=4.8 Hz, 2H) 5.32 (quin, J=6.6 Hz, 1H), 5.90 (s, 1H), 8.00 (s, 1H), 8.23 (d, J=9.4 Hz, 1H), 8.54-8.64 (m, 1H), 8.79 (t, J=4.7 Hz, 1H), 8.91 (s, 1H), 11.54 (br. s., 1H).

Provenance & Evidence