Sodium hydride → 1-(3,6-dibromo-9H-carbazol-9-yl)-4-(phenylamino)butan-2-ol

HRID 62158

Reaktionsgleichung

Reaktionsgleichung von HRID 62158
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.[O:18]1[CH2:20][CH:19]1[CH2:21][CH2:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:20][CH:19]([OH:18])[CH2:21][CH2:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2748743,6-DibromocarbazoleHCID 18628254N-(2-(oxiran-2-yl)ethyl)aniline

Produkt 1

HCID 468512131-(3,6-dibromo-9H-carbazol-9-yl)-4-(phenylamino)butan-2-olAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

NaH (60% dispersed in mineral oil, 0.0018 g, 0.0452 mmol) was added to a solution of 3,6-dibromocarbazole (0.0147 g, 0.0452 mmol) in 0.5 mL anhydrous THF and the mixture was stirred for 15 min. N-(2-(oxiran-2-yl)ethyl)aniline (0.0067 g, 0.0410 mmol) in 1.5 mL anhydrous THF solution was added dropwise and the resulting mixture was stirred at 60° C. overnight. THF was removed under vacuum and the residue was dissolved in 10 mL EtOAc and washed with water 2×5 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0115 g colorless oil; yield 57.5%.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 60° C. overnight
  2. customTHF was removed under vacuum
  3. dissolutionthe residue was dissolved in 10 mL EtOAc
  4. washwashed with water 2×5 mL
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customevaporated
  7. customto afford the crude product, which

Quellen und Nachweise

ORD-Eintrag
ord-ff447b6d34764a3a8936fee5d44df5d1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446022B2

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