Methyl iodide → Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylate

HRID 244615노트

반응식

HRID 244615 반응식
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C.O.C(Cl)Cl>[CH3:11][N:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[CH:3]=[N:4]1

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3467807Methyl 4-methyl-1H-pyrazole-3-carboxylate

생성물 1

HCID 20718564Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylate수율 31.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Methyl 4-methyl-1H-pyrazole-5-carboxylate (0.5 g) and cesium carbonate (1.16 g) were dissolved in acetonitrile (10 ml). Methyl iodide (0.25 ml) was added and the mixture stirred at RT for 16 h. The reaction mixture was diluted with water (20 ml) and DCM (20 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with DCM (2×20 ml) using a hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound (0.172 g) as a colourless oil.

후처리

  1. customseparated
  2. extractionThe aqueous layer was extracted with DCM (2×20 ml)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-366bb9393deb4a7ebef3a57a10006196
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658635B2

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