Pyridine → ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylate

HRID 925411노트

반응식

HRID 925411 반응식
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19](B(O)O)[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]([C:17]2[CH:16]=[C:15]([Cl:14])[CH:20]=[CH:19][C:18]=2[CH3:24])[N:5]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 162204305-Acetyl-2H-pyrazole-3-carboxylic acid ethyl ester

생성물 1

HCID 70873383ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylate수율 43.8%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of ethyl 3-acetyl-1H-pyrazole-5-carboxylate (364 mg, 2.0 mmol), (5-chloro-2-methylphenyl)boronic acid (680 mg, 4.0 mmol), copper(II) acetate (571 mg, 3.0 mmol) and pyridine (0.32 mL, 4 mmol) in DCM (10 mL) was stirred at r.t. under an air atmosphere for 48 h. After removal of the insolubles by filtration, the filtrate was washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (hexane/AcOEt, 90/10) to obtain ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylate as a white solid (269 mg, 43%),

후처리

  1. customAfter removal of the insolubles
  2. filtrationby filtration
  3. washthe filtrate was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (hexane/AcOEt, 90/10)

출처 및 근거

ORD 기록
ord-8ef16a13ab8e48d197f7c9467306f6f1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284298B2

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