반응 #158295

반응 방정식

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

용매

DMF

water

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The extract was washed with saturated brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   기타the 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
    추출the mixture was extracted with ethyl acetate
12. 12
    세척The extract was washed with saturated brine
13. 13
    건조dried over anhydrous magnesium sulfate
14. 14
    기타the solvent was evaporated under reduced pressure
15. 15
    기타The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

실험 절차

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).

출처