(2-Bromoethoxy)-tert-butyldimethylsilane → 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-6-nitro-1H-indazole

HRID 386655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386655
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][N:6]=[CH:5]2.C[Si](C)(C)N[Si](C)(C)C.[Li].Br[CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C=O)C>[C:31]([Si:28]([CH3:30])([CH3:29])[O:27][CH2:26][CH2:25][N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=2)[CH:5]=[N:6]1)([CH3:34])([CH3:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 126378375-methyl-6-nitro-1H-indazoleHCID 57426343Lithium bis(trimethylsilyl)amide

Produkt 1

HCID 582002841-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-6-nitro-1H-indazoleAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Methyl-6-nitro-1H-indazole (354 mg, 2.0 mmol) was dissolved in DMF (10 ml) and the mixture was cooled to 0° C. with stirring. Lithium hexamethyldisilazane (2.2 ml of 1.0 M toluene solution) was added dropwise. The mixture was allowed to stir for five minutes, and then (2-bromoethoxy)-tert-butyldimethylsilane (0.52 ml, 2.4 mmol) was added. The mixture was stirred for 30 minutes at 0° C., then allowed to warm to room temperature with stirring for four hours. The reaction was quenched with pH2 buffer solution, and the mixture was then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 4:1 hexanes/ethyl acetate) to give 340 mg (50.7%) of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-6-nitro-1H-indazole as a white powder.

Aufarbeitung

  1. stirringto stir for five minutes
  2. stirringThe mixture was stirred for 30 minutes at 0° C.
  3. temperatureto warm to room temperature
  4. stirringwith stirring for four hours
  5. customThe reaction was quenched with pH2 buffer solution
  6. extractionthe mixture was then extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography (gradient 9:1 to 4:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-56568e8184294b0fb7f5063be40d6316
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372865B2

Notizen zur Reaktion

Wird geladen…