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(Diethylamino)sulfur trifluoride → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

HRID 404272
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 404272
CCN(S(F)(F)[F:7])CC.[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:25][CH:26](O)[CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=3>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:25][CH:26]([F:7])[CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=3
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 3103961P7C3-OMe

Produkt 1

HCID 46853447N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyanilineAusbeute 5,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

DAST [(Et2NSF3) 0.12 ml, 0.916 mmol] was added dropwise to a solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (0.102 g, 0.203 mmol) in 6.0 ml of anhydrous DCM at −78° C. The reaction was stirred at −78° C. for one hour before being slowly warmed to 0° C. over 5 hours. The reaction was quenched by addition of phosphate buffer (pH=8) and extracted with DCM. The aqueous phase was extracted twice with 10 ml DCM. The combined organics were dried over Na2SO4, filtered and concentrated. The crude reaction material was purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA). Fractions containing the desired fluorinated product were further purified with 40% EtOAc/hexanes (+0.1% TEA). Isolated 5.7 mg desired product.

Aufarbeitung

  1. temperaturebefore being slowly warmed to 0° C. over 5 hours
  2. customThe reaction was quenched by addition of phosphate buffer (pH=8)
  3. extractionextracted with DCM
  4. extractionThe aqueous phase was extracted twice with 10 ml DCM
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude reaction material
  9. customwas purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA)
  10. additionFractions containing the
  11. customwere further purified with 40% EtOAc/hexanes (+0.1% TEA)

Quellen und Nachweise

ORD-Eintrag
ord-0f860566e9b745dab85ed1dba46f2d47
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08748473B2

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