Reaktion #683111

Reaktionsgleichung

triphenylphosphine

iodine

imidazole

(4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol

→

2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine

Ausbeute 60.6%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated to 60° C. in an oil bath for 48 h
2. 2
   FiltrationSolid was filtered off
3. 3
   Sonstigethe filtrate was purified by flash column chromatography on silicagel (ISCO)
4. 4
   Wascheneluting with 0-80% ethyl acetate in heptane
5. 5
   Sonstigeto give

Vorschrift

To an ice cooled solution of triphenylphosphine (983 mg, 3.75 mmol), iodine (952 mg, 3.75 mmol) in dichloromethane (20 mL) was added imidazole (278 mg, 4.09 mmol). The solution was stirred at ambient temperature for 1 h, followed by the addition of (4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol (360 mg, 1.70 mmol) in 10 mL dichloromethane. The reaction mixture was heated to 60° C. in an oil bath for 48 h. Solid was filtered off, the filtrate was purified by flash column chromatography on silicagel (ISCO) eluting with 0-80% ethyl acetate in heptane to give to give 2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine (330 mg, 1.03 mmol, 60.3% yield) as light yellow color oil. LCMS (m/z): 322 (MH+), 0.77 min.

Quelle