反応 #158342

ord-c8fce6d06f5245a9ba815595f6135105

反応方程式

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
収率 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
収率 50.9%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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).

出典

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