Sodium Bicarbonate → HCID 56597156, compound

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]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (80 mg, 0.21 mmol), [4-(aminocarbonyl)phenyl]boronic acid (52.9 mg, 0.31 mmol), bis(triphenylphosphine)palladium(II) chloride (8.7 mg, 0.01 mmol), DME/water (4 mL, 3:1) and sodium bicarbonate (54 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 0 to 90:10:1). The collected solid was suspended in EtOH, sonicated, and filtered. After further washing with EtOH/DCM, the filtered 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)=459.3 1H NMR (400 MHz, DMSO-d6) δ ppm 11.58 (s, 1H) 9.00 (t, J=4.93 Hz, 1H) 8.41 (s, 1H) 8.36 (s, 1H) 8.34 (s, 1H) 8.24 (s, 1H) 8.13 (s, 1H) 8.06 (s, 1H) 8.04 (s, 1H) 7.51 (s, 1H) 5.91 (s, 1H) 5.37 (quin, J=6.69 Hz, 1H) 4.42 (d, J=4.80 Hz, 2H) 2.23 (s, 3H) 2.13 (s, 3H) 1.56 (s, 3H) 1.55 (s, 3H).

Provenance & Evidence