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Imidazole → 8-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

HRID 1391669
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1391669
[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][C:12]([OH:18])=[CH:11][CH:10]=4.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([Si:28]([CH3:30])([CH3:29])[O:18][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:17][CH2:16][C:15]2=1)([CH3:27])([CH3:26])[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 444118686,11-Dihydrothiochromeno[4,3-b]indol-8-ol

Produkt 1

HCID 596760598-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-ol (820 mg, 3.24 mmoL) in DMF (10 mL) was treated with imidazole (331 mg, 4.862 mmoL) followed by TBSCl (733 mg, 4.862 mmoL) at room temperature. The reaction was stirred for 2 hours. The reaction mixture was then partitioned between CH2Cl2 and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent) to yield the title compound as a brown solid.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between CH2Cl2 and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-fc1a3da884b14bf189ae1fa687eff70f
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07338973B2

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