Sodium Iodide → HCID 66955311, Verbindung

HRID 539640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539640
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)[CH:3]=1.Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CN1C(=O)CCC1.CCOC(C)=O>[C:24]([Si:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][N:6]1[C:2]([CH3:1])=[CH:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[N:5]1)([CH3:27])([CH3:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 593775315-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole

Produkt 1

HCID 66955311HCID 66955311, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 5-Methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole, 2-bromoethoxy tertbutyldimethylsilane, Cs2CO3 and NaI in NMP was heated in a microwave oven at 100° C. for 1 hour, and then cooled to room temperature. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes to give 867 mg of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole as an oil that also contained 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-5-(4-methyl-3-nitro-phenyl)-1H-pyrazole as a minor product.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-07441ab4a2eb413e831d70ca22c0bc08
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871760B2

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