Reaktion #158310

Reaktionsgleichung

ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

DMF

sodium hydride

Sodium hydride

1-bromo-2-(bromomethyl)-4-fluorobenzene

ammonium chloride

→

title compound

ethyl 8-[(2-bromo-5-fluorobenzyl)oxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To a mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1000 mg) in DMF (8 mL) was added sodium hydride (60%, 115 mg), and the mixture was stirred at room temperature for 1 hr in the air. Sodium hydride (60%, 115 mg) and 1-bromo-2-(bromomethyl)-4-fluorobenzene (1051 mg) were added, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (920 mg).

Quelle