反应 #158342

ord-c8fce6d06f5245a9ba815595f6135105

反应方程式

O=C([O-])O.[Na+]
sodium hydrogen carbonate
CCOC(=O)C1(Cl)CCCn2c(-c3ccc(-c4cnc(C)o4)c(OC)c3)nnc21
Ethyl 8-chloro-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
Oc1cccc(C(F)(F)F)c1
3-(trifluoromethyl)phenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)C1(Oc2cccc(C(F)(F)F)c2)CCCn2c(-c3ccc(-c4cnc(C)o4)c(OC)c3)nnc21
title compound
收率 50.9%
CCOC(=O)C1(Oc2cccc(C(F)(F)F)c2)CCCn2c(-c3ccc(-c4cnc(C)o4)c(OC)c3)nnc21
ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate
收率 50.9%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取the mixture was extracted with ethyl acetate
  2. 2
    洗涤The extract was washed with saturated brine
  3. 3
    干燥dried over anhydrous sodium sulfate
  4. 4
    其他the solvent was evaporated under reduced pressure
  5. 5
    其他The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

实验过程

Ethyl 8-chloro-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 (1.0 g) was added to a mixture of 3-(trifluoromethyl)phenol (408 mg), potassium carbonate (995 mg) and DMF (10 mL) at 90° C., and the mixture was stirred for 30 min. Saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was 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 (ethyl acetate/hexane) to give the title compound (663 mg).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08822699B2uspto-grants-2014_09