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

HRID 2095845ノート

反応式

HRID 2095845 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b520fbdbf9d44642b3d09afd7f3b9953
出典データセット
uspto-grants-2013_05
特許番号
US08445509B2

反応ノート

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