反应详情

A solution of dimethyl zinc (1.73 ml, 3.46 mmol) was added dropwise to a mixture of 3-iodo-4-nitro-1H-indazole (0.500 g, 1.73 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (0.427 g, 0.519 mmol) in dioxane (0.2M, 9 mL) under argon. The mixture was heated under reflux for 2 hours. After cooling, MeOH (<1 mL) was added, followed by 2N HCl (1 mL) and DCM (5 mL). After stirring mixture for 30 minutes, the organic layer was separated, washed with saturated aqueous sodium bicarbonate, water, and brine. The combined organic extracts were dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (1-10% EtOAc in DCM to provide 3-methyl-4-nitro-1H-indazole (0.082 g, 27% yield) as a brown residue.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 2 hours
3. temperatureAfter cooling
4. customthe organic layer was separated
5. washwashed with saturated aqueous sodium bicarbonate, water, and brine
6. customThe combined organic extracts were dried
7. addition(phase separator silicone treated filter paper)
8. concentrationconcentrated
9. custompurified on silica gel (1-10% EtOAc in DCM