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

HRID 1874331

반응식

HRID 1874331 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1c241cf46da14c0381c4372822fb42e4
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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