Sodium Bicarbonate → 6-[4-(Acetylamino)phenyl]-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 93 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 (80 mg, 0.21 mmol), [4-(acetylamino)phenyl]boronic acid (55.4 mg, 0.31 mmol), bis(triphenylphosphine)palladium(II) chloride (8.4 mg, 0.01 mmol), DME/water (4 mL, 3:1) and sodium bicarbonate (52 mg, 0.62 mmol). The crude product was dissolved in DCM/MeOH (1:1) and preabsorbed onto silica gel. The product was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH. gradient of 0 to 80:20:2). The collected solid was suspended in EtOH/EtOAc (1:1), sonicated, and filtered. After further washing with hexanes, the solid was then air-dried for 15 min, and then in vacuum oven overnight. The final product was collected as 70 mg (69%). LCMS E-S (M+H)=487.3 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (br. s., 1H) 10.16 (s, 1H) 8.73 (t, J=5.05 Hz, 1H) 8.17 (m, J=8.84 Hz, 2H) 7.74 (m, J=8.84 Hz, 2H) 7.64 (s, 1H) 5.89 (s, 1H) 5.25 (quin, J=6.69 Hz, 1H) 4.39 (d, J=4.80 Hz, 2H) 2.43 (s, 3H) 2.25 (s, 3H) 2.12 (s, 3H) 2.09 (s, 3H) 1.51 (s, 3H) 1.49 (s, 3H).

Provenance & Evidence