Cesium carbonate → N-[6-(2-fluoro-4-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095793

반응식

HRID 2095793 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[CH:7]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[F:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:15][CH2:16]3)=[O:13])[N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 57749397N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

생성물 1

HCID 58158626N-[6-(2-fluoro-4-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide수율 46%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (2 g, 9.16 mmol) and 1,2-difluoro-4-nitrobenzene (1.46 g, 9.16 mmol) in dimethyl sulfoxide (20 mL) was added cesium carbonate (4.48 g, 13.7 mmol), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was filtered through celite, and the filtrate was diluted with water and ethyl acetate, and extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (1.5 g, 46%) as a white solid.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. additionthe filtrate was diluted with water and ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate

출처 및 근거

ORD 기록
ord-88bd717f85134423bdc98d0d2c74a780
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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