Ethanol → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

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Reaction Steps

To a 50 mL round bottom flask fitted with a 3-way inlet was placed 10% Pd/C (0.071 g, 0.033 mmol) followed by degassing with N2, and then addition of 2 mL ethanol. Added next to the stirring slurry was 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 (0.25 g, 0.669 mmol). Additional ethanol (8 mL) and THF (10 mL) were added with slight warming to facilitate dissolution. The stirring contents were allowed to cool (15 min.) then fitted with a balloon of H2 and allowed to stir at room temperature overnight. The contents were then purged with N2. The mixture was then diluted with 10% MeOH/DCM (20 mL), stirred for 10 min., and filtered through Celite. The filtrate was concentrated in vacuo and the crude solid was triturated with ethanol. After filtration and washing the collected solid with additional ethanol (cold), the solid was air-dried for 15 min, then in vacuum oven at 40° C. overnight. The final product was collected as 185 mg (80%). LCMS E-S (M+H)=340.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, J=6.82 Hz, 6H), 2.13 (s, 3H), 2.22 (s, 3H), 4.37 (d, J=4.80 Hz, 2H), 5.18-5.31 (m, 1H), 5.89 (s, 1H), 7.54 (d, J=4.80 Hz, 1H), 8.36 (s, 1H), 8.63 (d, J=4.55 Hz, 1H), 8.82 (t, J=4.93 Hz, 1H), 11.56 (s, 1H).

Provenance & Evidence