反応 #80174

反応方程式

4-bromo-2-nitro-anisole

methyl-(tetrahydro-pyran-4-yl)-amine hydrochloride

2-(dicyclohexylphosphino)biphenyl

cesium carbonate

→

(4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-yl)-amine

収率 18.5%

溶媒

dioxane

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux for 72 h
3. 3
   workup.ADDITIONpoured onto water
4. 4
   抽出extracted three times with ethyl acetate
5. 5
   乾燥The combined organic phases were dried over sodium sulfate
6. 6
   濃縮concentrated in vacuo

実験手順

To a stirred solution of 7.50 g (32.0(mmol) 4-bromo-2-nitro-anisole in 200 ml dioxane were added 6.86 g (45.0 mmol) methyl-(tetrahydro-pyran-4-yl)-amine hydrochloride (1:1), 1.13 g (3.0 mmol) 2-(dicyclohexylphosphino)biphenyl, 14.75 g (45.0 mmol) cesium carbonate, and 360 mg (2.0 mmol) palladium (II) acetate. The mixture was heated at reflux for 72 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/2 hexane/ethyl acetate) afforded 1.59 g (18.5%) (4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-yl)-amine as a red solid. ES-MS m/e (%): 267 (M+H+, 100).

出典