تفاعل #1828913

معادلة التفاعل

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

المذيبات

DMF

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةTo a cooled
2. 2
   أخرىThe reaction mixture is then partitioned between water (200 mL) and EtOAc (200 mL)
3. 3
   استخلاصThe aqueous layer is extracted with EtOAc (1×200 mL)
4. 4
   غسيلThe combined organic extracts are then washed with H2O (4×200 mL), saturated NaCl solution (2×200 mL)
5. 5
   تجفيفdried over MgSO4
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe resulting material is chromatographed (silica gel. 1:4 EtOAc-hexanes)

الإجراء التجريبي

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.

المصدر