Methyl iodide → HCID 69356057, Verbindung

HRID 1064079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064079
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[C:16](=[O:32])[NH:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Li+].I[CH3:36]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[C:16]([O:32][CH3:36])=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 62714Lithium hydrideHCID 69357048HCID 69357048, Verbindung

Produkt 1

HCID 69356057HCID 69356057, VerbindungAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-[4-(4-chlorophenyl)-3-oxo-5-pyridin-4-yl-2,3-dihydro-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.135 g, 0.3 mmol) in dry DMF (2 mL) was cooled to 0° C. and added lithium hydride (0.0035 g, 0.45 mmol). After stirring for 5 minutes, iodomethane (0.037 mL, 0.6 mmol) was added and the reaction was allowed to gradually warmed to room temperature and stirred for 20 hours. The reaction was diluted with ethyl acetate and washed with water; the aqueous layer was back-washed with ethyl acetate. The combined organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. Flash chromatography with 1%, 3%, and 5% methanol/methylene chloride afforded 18.8 mg (13%) of a monomethylated product. MS (ES+): 469.2 (M+H)+.

Aufarbeitung

  1. stirringstirred for 20 hours
  2. washwashed with water
  3. washthe aqueous layer was back-washed with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a48fdbfb48fc4cc4bd4692452ec1f3cd
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967254B2

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