Reacción #1828913

Ecuación de reacción

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

Disolventes

DMF

DMF

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente