4-((Tert-butyldimethylsilyl)oxy)aniline → N-[4-[tert-Butyl(dimethyl)silyl]oxyphenyl]-1-(oxetan-3-yl)-1H-pyrazol-4-amine

HRID 515905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515905
[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[N:19][N:20]([CH:22]2[CH2:25][O:24][CH2:23]2)[CH:21]=1>O1CCCC1>[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:25][O:24][CH2:23]3)[CH:21]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 739778714-Bromo-1-(oxetan-3-YL)-1H-pyrazole

Produkt 1

HCID 131733317N-[4-[tert-Butyl(dimethyl)silyl]oxyphenyl]-1-(oxetan-3-yl)-1H-pyrazol-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-[tert-Butyl(dimethyl)silyl]oxyaniline (1.5 g, 7.2 mmol) and 4-bromo-1-(oxetan-3-yl)-pyrazole (1.6 g, 7.2 mmol) dissolved in anhydrous tetrahydrofuran (25 mL) are stirred for 3 hours at ambient temperature in the presence of sodium tert-butylate (3.7 mL, 2M solution in THF) and chloro(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) (101 mg, 0.145 mmol). The reaction mixture is filtered over Celite and then evaporated to dryness. The residue is purified by chromatography over silica gel using dichloromethane containing diethylamine and ethyl acetate as eluants to yield the expected product.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered over Celite
  2. customevaporated to dryness
  3. customThe residue is purified by chromatography over silica gel
  4. additioncontaining diethylamine and ethyl acetate as eluants

Quellen und Nachweise

ORD-Eintrag
ord-3e1116e6e3934d9b9e83ed392f54f5de
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108983B2

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