反应 #166440

反应方程式

dichloromethane

diethylzinc

1-benzyl-3-iodo-4-nitro-1H-indazole

methanol

→

1-benzyl-3-ethyl-4-nitro-1H-indazole

收率 20.4%

溶剂

dioxane

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   其他The mixture was transferred to a separatory funnel
5. 5
   洗涤washed with water (30 mL)
6. 6
   干燥The organic phase was dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated under vacuum
9. 9
   其他The crude product was purified by column chromatography on silica
10. 10
    洗涤eluting with 15-20% ethyl acetate in hexanes
11. 11
    workup.ADDITIONFractions containing product
12. 12
    浓缩were concentrated under reduced pressure

实验过程

To a mixture of 1-benzyl-3-iodo-4-nitro-1H-indazole (304 mg, 0.802 mmol) (prepared as in Example 1, steps E-F) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (196 mg, 0.241 mmol) in dioxane (4.0 mL) under an atmosphere of dry nitrogen was added a solution of diethylzinc (1.6 mL, 1.60 mmol; 1 molar in hexane) with magnetic stirring. The mixture was heated at reflux for 2 hours. After allowing to cool methanol (1 mL) was added followed by dichloromethane (30 mL) and the mixture was stirred for 30 minutes. The mixture was transferred to a separatory funnel and washed with water (30 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica, eluting with 15-20% ethyl acetate in hexanes. Fractions containing product were concentrated under reduced pressure to give 1-benzyl-3-ethyl-4-nitro-1H-indazole (46 mg).

来源