Phenethyl bromide → Methyl 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylate

HRID 547506노트

반응식

HRID 547506 반응식
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][NH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 178499180HCID 178499180, 화합물

생성물 1

HCID 67198071Methyl 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylate수율 65.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

430 mg (2.5 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.41 ml (3 mM) of (2-bromoethyl)benzene and 1.6 g (5.0 mM) of cesium carbonate were added dropwise, and the mixture was stirred under a nitrogen atmosphere for a day. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1), to obtain 506 mg (65.5%) of the title compound and 218 mg (31.2%) of the compound of Preparative Example 10.

후처리

  1. additionwere added dropwise
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-d54ff581a1bb495986f13fc1ec59049e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939550B2

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