Reaktion #1828913

Reaktionsgleichung

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

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo a cooled
2. 2
   SonstigeThe reaction mixture is then partitioned between water (200 mL) and EtOAc (200 mL)
3. 3
   ExtraktionThe aqueous layer is extracted with EtOAc (1×200 mL)
4. 4
   WaschenThe combined organic extracts are then washed with H2O (4×200 mL), saturated NaCl solution (2×200 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe resulting material is chromatographed (silica gel. 1:4 EtOAc-hexanes)

Vorschrift

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.

Quelle