Ethyl Acetate → N-{6-[(5-nitropyridin-2-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 2095845노트

반응식

HRID 2095845 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[CH:7]=1.Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O.O.O1CCCC1>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:1][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]4[CH2:15][CH2:16]4)=[O:13])[N:10]=3)[CH:7]=2)=[N:19][CH:20]=1)([O-:26])=[O:25]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 783082-Chloro-5-nitropyridineHCID 58158532N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

생성물 1

HCID 58158519N-{6-[(5-nitropyridin-2-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide수율 36%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-(6-hydroxyimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide (200 mg, 0.921 mmol) and 2-chloro-5-nitropyridine (175 mg, 1.1 mmol) in dimethyl sulfoxide (3 mL) was added cesium carbonate (450 mg, 1.38 mmol), and the mixture was stirred at room temperature for 3 hr. Ethyl acetate, tetrahydrofuran and water were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (111 mg, 36%) as a brown solid.

후처리

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate
  7. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-b520fbdbf9d44642b3d09afd7f3b9953
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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