Dimethylformamide → 1,3-dimethyl-N-{2-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

HRID 1874331

反応式

HRID 1874331 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[CH:12]=2)=[O:10])[CH:7]=1.Br[C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[N:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH3:16][N:15]1[C:11]([C:9]([NH:8][C:6]2[CH:7]=[C:2]([O:1][C:20]3[CH:25]=[N:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)[CH:3]=[CH:4][C:5]=2[CH3:18])=[O:10])=[CH:12][C:13]([CH3:17])=[N:14]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 57505436N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 577493301,3-dimethyl-N-{2-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide収率 50.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (4.67 g, 19.0 mmol), 5-bromo-2-nitropyridine (3.68 g, 18.1 mmol), cesium carbonate (9.29 g, 28.5 mmol) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→0/100) and then column chromatography (NH silica gel, hexane/ethyl acetate=80/20→0/100) to give the title compound (3.38 g, 44%) as a white solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20→0/100)

出典と根拠

ORDレコード
ord-1c241cf46da14c0381c4372822fb42e4
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

関連ノート

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