Sodium Carbonate → 6-(2-Amino-6-quinazolinyl)-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 28 mg (31%). LCMS E-S (M+H)=497.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (d, J=6.8 Hz, 6H), 2.12 (s, 3H), 2.26 (s, 3H), 4.41 (d, J=5.0 Hz, 2H) 5.30 (quin, J=6.6 Hz, 1H), 5.89 (s, 1H), 7.16 (br. s., 2H), 7.56 (d, J=9.1 Hz, 1H), 7.78 (s, 1H) 8.60 (dd, J=8.8, 2.0 Hz, 1H), 8.69 (d, J=1.8 Hz, 1H), 8.76 (t, J=4.9 Hz, 1H), 9.28 (s, 1H), 11.53 (s, 1H).

Provenance & Evidence