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

HRID 925411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925411
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 70873383ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylateAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%),

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8ef16a13ab8e48d197f7c9467306f6f1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284298B2

Notizen zur Reaktion

Wird geladen…