Реакция #158295

Уравнение реакции

8-(3,4-dichlorophenyl)-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

sodium hydride

(2-Bromoethoxy)(tert-butyl)dimethylsilane

→

title compound

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

Растворители

DMF

water

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
3. 3
   Экстракцияthe mixture was extracted with ethyl acetate
4. 4
   ПромывкаThe extract was washed with saturated brine
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was evaporated under reduced pressure
7. 7
   workup.ADDITIONTo a mixture of the residue in THF (2 mL)
8. 8
   workup.ADDITIONwas added TBAF (1M THF solution, 439 μL)
9. 9
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hr
10. 10
    workup.ADDITIONThe reaction mixture was diluted with water
11. 11
    Экстракцияthe mixture was extracted with ethyl acetate
12. 12
    ПромывкаThe extract was washed with saturated brine
13. 13
    Сушкаdried over anhydrous magnesium sulfate
14. 14
    Другоеthe solvent was evaporated under reduced pressure
15. 15
    ДругоеThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Методика

To a mixture of 8-(3,4-dichlorophenyl)-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 (200 mg) in DMF (5 mL) was added sodium hydride (60%, 31.6 mg) under ice-cooling, and the mixture was stirred for 30 min under a nitrogen atmosphere. (2-Bromoethoxy)(tert-butyl)dimethylsilane (113 μL) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a mixture of the residue in THF (2 mL) was added TBAF (1M THF solution, 439 μL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (26.9 mg).

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