Réaction #1828913

Équation de réaction

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

Solvants

DMF

DMF

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source