Potassium Iodide → 9-(2-hydroxy-2-methyl-3-phenoxypropyl)-9H-carbazole-3,6-dicarbonitrile

HRID 1028315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028315
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17]([CH3:27])([OH:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[C-:28]#[N:29].[Na+].[I-].[K+].[CH3:33][N:34](C)CCN>[Cu](I)I.C1(C)C=CC=CC=1>[OH:26][C:17]([CH3:27])([CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:33]#[N:34])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([C:28]#[N:29])[CH:14]=2

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 66053N,N-DimethylethylenediamineHCID 71253947HCID 71253947, Verbindung

Produkt 1

HCID 712540929-(2-hydroxy-2-methyl-3-phenoxypropyl)-9H-carbazole-3,6-dicarbonitrileAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

An oven dried vial was charged with 1-(3,6-dibromo-9H-carbazol-9-yl)-2-methyl-3-phenoxypropan-2-ol (79.5 mg, 0.16 mmol), copper iodide (16 mg, 0.08 mmol), sodium cyanide (22 mg, 0.45 mmol) and potassium iodide (16 mg, 0.10 mmol). The sealed vial was nitrogen filled and evacuated three times before addition of N, N-dimethyl-1,2-ethanediamine (22.5 μl, 0.21 mmol) and anhydrous toluene (75 μl). The reaction was heated at 100° C. over 60 hours. The cooled mixture was diluted with EtOac, washed with water and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified on silica gel in 40% THF/hexanes. Yield=34%.

Aufarbeitung

  1. customAn oven dried vial
  2. additionfilled
  3. customevacuated three times
  4. additionThe cooled mixture was diluted with EtOac
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe crude mixture was purified on silica gel in 40% THF/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-80c73f41004e48f7ae5e7c2cf85f6afa
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735440B2

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