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Dimethylacetamide → 9-((R)-2,3-Dihydroxy-propoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275186
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2275186
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:30])[C:8]4[CH:20]=[C:19]([O:21][CH2:22][C@H:23]5[CH2:27][O:26]C(C)(C)[O:24]5)[CH:18]=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[Cu](C#N)[C:32]#[N:33].CC(N(C)C)=O>O>[OH:24][C@H:23]([CH2:27][OH:26])[CH2:22][O:21][C:19]1[CH:18]=[CH:17][C:9]2[C:10]([CH3:15])([CH3:16])[C:11]3[NH:12][C:13]4[C:5]([C:6]=3[C:7](=[O:30])[C:8]=2[CH:20]=1)=[CH:4][CH:3]=[C:2]([C:32]#[N:33])[CH:14]=4
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 668343293-Bromo-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 668350169-((R)-2,3-Dihydroxy-propoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

3-Bromo-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound JJ3-1, 49.5 mg, 0.105 mmol) and copper cyanide (90%, 35.3 mg, 3.4 eq.) were added with DMA (0.5 mL), and the mixture was irradiated with microwave at 200° C. for 1 hr under nitrogen atmosphere. After cooling, the reaction solution was added with water and extracted with ethyl acetate. The insoluble matters were separated off by filtration, and the organic layer was washed with brine and dried over magnesium sulfate. After filtration and the concentration under reduced pressure, the resulting residues were purified by preparative TLC (methanol/dichloromethane) to obtain the title compound (white solid, 8.5 mg, 22%).

Aufarbeitung

  1. customthe mixture was irradiated with microwave at 200° C. for 1 hr under nitrogen atmosphere
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customThe insoluble matters were separated off by filtration
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe concentration under reduced pressure
  9. customthe resulting residues were purified by preparative TLC (methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-703a1cb331d74cc7a64eceec5ef87514
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09126931B2

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