反应详情

A solution of 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (Example 89, Steps A-B; 1.00 g, 2.54 mmol) in MeOH (25 mL) was cooled to 0° C. Zinc dust (0.829 g, 12.7 mmol) was added and the mixture was stirred for 10 minutes. Saturated aqueous NH4Cl was added (25 mL) and the mixture was stirred vigorously for 2 hours at 0° C. and then warmed to ambient temperature and stirred for an additional 2 hours. Additional saturated aqueous NH4Cl was added (12.5 mL) and the mixture was stirred at ambient temperature for an additional 2 hours. The mixture was diluted with MeOH and filtered. To the filtrate was added saturated aqueous NH4OAc and the mixture was concentrated to remove bulk MeOH. The mixture was then extracted with EtOAc and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography (2 to 20% IPA/CHCl3) to afford 0.428 g (70%) of the desired product as an orange solid.

1. stirringthe mixture was stirred vigorously for 2 hours at 0° C.
2. stirringstirred for an additional 2 hours
3. stirringthe mixture was stirred at ambient temperature for an additional 2 hours
4. filtrationfiltered
5. additionTo the filtrate was added saturated aqueous NH4OAc
6. concentrationthe mixture was concentrated
7. customto remove bulk MeOH
8. extractionThe mixture was then extracted with EtOAc
9. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude material was purified by column chromatography (2 to 20% IPA/CHCl3)