反应详情

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).

1. customTo a 50 mL round bottom flask fitted with a 3-way inlet
2. customby degassing with N2
3. additionaddition of 2 mL ethanol
4. additionAdded next to the stirring slurry
5. temperaturewith slight warming
6. dissolutiondissolution
7. temperatureto cool (15 min.)
8. customthen fitted with a balloon of H2
9. customThe contents were then purged with N2
10. additionThe mixture was then diluted with 10% MeOH/DCM (20 mL)
11. stirringstirred for 10 min.
12. filtrationfiltered through Celite
13. concentrationThe filtrate was concentrated in vacuo
14. customthe crude solid was triturated with ethanol
15. filtrationAfter filtration
16. washwashing the collected solid with additional ethanol (cold)
17. customthe solid was air-dried for 15 min
18. customat 40° C.
19. customovernight
20. customThe final product was collected as 185 mg (80%)