Pyridine → HCID 66777713, Verbindung

HRID 2090938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090938
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:5]2[CH:6]=[C:2]([CH3:1])[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 178470484HCID 178470484, Verbindung

Produkt 1

HCID 66777713HCID 66777713, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Ethyl 4-methyl-1H-pyrazole-3-carboxylate (2.58 g) was dissolved in N,N-dimethylacetamide (50 mL), 4-methoxyphenylboronic acid (5.0 g), copper acetate (6.0°g) and pyridine (5.3 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL) was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (2.7 g, 66%) as a pale-yellow oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL)
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-6dd3f7b026914665b83894d49ed7b547
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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