تفاعل #166440

معادلة التفاعل

dichloromethane

diethylzinc

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

methanol

→

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

المردود 20.4%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   أخرىThe mixture was transferred to a separatory funnel
5. 5
   غسيلwashed with water (30 mL)
6. 6
   تجفيفThe organic phase was dried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىThe crude product was purified by column chromatography on silica
10. 10
    غسيلeluting with 15-20% ethyl acetate in hexanes
11. 11
    workup.ADDITIONFractions containing product
12. 12
    تركيزwere concentrated under reduced pressure

الإجراء التجريبي

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).

المصدر