Reaktion #2161288

Reaktionsgleichung

Methoxyethylbromide

4-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]pyridine

NaH

→

title compound

Ausbeute 60.2%

4-(5-(4-fluorobenzyl)-1-(2-methoxyethyl)-1H-pyrazol-3-yl)pyridine

Ausbeute 60.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   Sonstigethe residue was purified by radial chromatography (2 mm plate, eluting with EtOAc)

Vorschrift

To a solution of 4-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]pyridine (0.122 g, 0.48 mmol) in DMF (3 ml) was added NaH (19 mg, 0.48 mmol) and the suspension was stirred for 20 minutes under nitrogen. Methoxyethylbromide (45 μL, 0.48 mmol) was then added and the reaction mixture was heated to 100° C. under nitrogen for 18 hours. The solvent was removed in vacuo and the residue was purified by radial chromatography (2 mm plate, eluting with EtOAc) to give the title compound as a clear oil (90 mg, 60%). 1H NMR (400 MHz, DICHLOROMETHANE-D2) δ ppm 8.54 (d, 2 H), 7.61 (d, 2 H), 7.18-7.24 (m, 2 H), 7.03 (t, 2 H), 6.32 (s, 1 H), 4.19 (t, 2 H), 4.05 (s, 2 H), 3.72 (t, 2 H), 3.28 (s, 3 H); m/z (APCI+) for C18H18N3FO 312.0 (M+H)+.

Quelle