反応 #1828913

反応方程式

NaH

5-(4-fluorophenyl)-2-(chloromethyl)pyridine

6-bromo-1-oxo-1,2,3,4-tetrahydroisoquinoline

→

6-bromo-2-{[5-(4-fluorophenyl)-2-pyridyl]methyl}-1-oxo-1,2,3,4 -tetrahydroisoquinoline

溶媒

DMF

DMF

DMF

反応条件

後処理

1. 1
   温度To a cooled
2. 2
   その他The reaction mixture is then partitioned between water (200 mL) and EtOAc (200 mL)
3. 3
   抽出The aqueous layer is extracted with EtOAc (1×200 mL)
4. 4
   洗浄The combined organic extracts are then washed with H2O (4×200 mL), saturated NaCl solution (2×200 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The resulting material is chromatographed (silica gel. 1:4 EtOAc-hexanes)

実験手順

To a cooled (0° C.) suspension of NaH (0.084 g. 3.5 mmol) and Kl (0.1 g, 0.6 mmol) in DMF (10 mL) is added dropwise a solution of 6-bromo-1-oxo-1,2,3,4-tetrahydroisoquinoline (0.65 g, 2.9 mmol) in DMF (10 mL). After 15 minutes, a solution of 5-(4-fluorophenyl)-2-(chloromethyl)pyridine (1.27 g, 5.8 mmol) in DMF (10 mL) is added dropwise and the resulting solution stirred for 12 hours. The reaction mixture is then partitioned between water (200 mL) and EtOAc (200 mL). The aqueous layer is extracted with EtOAc (1×200 mL). The combined organic extracts are then washed with H2O (4×200 mL), saturated NaCl solution (2×200 mL), and dried over MgSO4 and concentrated in vacuo. The resulting material is chromatographed (silica gel. 1:4 EtOAc-hexanes) to afford 6-bromo-2-{[5-(4-fluorophenyl)-2-pyridyl]methyl}-1-oxo-1,2,3,4 -tetrahydroisoquinoline as pale yellow oil.

出典