反応 #158371

反応方程式

hydrochloric acid

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

(trifluoromethyl)trimethylsilane

TBAF

→

title compound

2,2,2-trifluoro-1-{3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}ethanol

溶媒

THF

sodium hydrogen carbonate

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   抽出the mixture was extracted with ethyl acetate
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他the solvent was evaporated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
8. 8
   その他further recrystallized from ethyl acetate/hexane

実験手順

To a mixture of 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carbaldehyde (150 mg) and (trifluoromethyl)trimethylsilane (0.137 mL) in THF (1.5 mL) was added TBAF (1M THF solution, 0.062 mL) under an argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for 2 hr, 1N hydrochloric acid (3 mL) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and further recrystallized from ethyl acetate/hexane to give the title compound (38.8 mg).

出典