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Potassium Iodide → 9-[8-(2,2,2-Trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-yl]-9H-xanthene-3-carbonitrile

HRID 733409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 733409
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:6]([CH:16]3[CH2:22][CH:21]4[N:23]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[Cu](C#N)[C:31]#[N:32].[I-].[K+]>CN(C=O)C>[F:27][C:25]([F:26])([F:28])[C:24]([N:23]1[CH:21]2[CH2:20][CH2:19][CH:18]1[CH2:17][CH:16]([CH:6]1[C:5]3[CH:4]=[CH:3][C:2]([C:31]#[N:32])=[CH:15][C:14]=3[O:13][C:12]3[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:22]2)=[O:29]
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Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 578392651-[3-(3-Bromo-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoroethanone2×HCID 178418260HCID 178418260, Verbindung2×

Produkt 1

HCID 578392559-[8-(2,2,2-Trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-yl]-9H-xanthene-3-carbonitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 1-[3-(3-bromo-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone, 2j (1.8 g, 3.86 mmol) in DMF (40 mL) was added copper cyanide (0.69 g, 7.72 mmol) and potassium iodide (50 mg), and the mixture was heated to reflux for 18 h. More copper cyanide (0.43 g) was added, and the mixture was heated to reflux for 30 h. The mixture was filtered and poured in ice-water. The solid was separated via filtration, washed with water, and air-dried. The crude product was purified via flash column chromatography (eluent gradient: 5% to 30% ethyl acetate in heptane) to yield 0.956 g (60%) of title compound 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-yl]-9H-xanthene-3-carbonitrile, 3j. MS m/z (MH+) 412.8.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 h
  5. filtrationThe mixture was filtered
  6. additionpoured in ice-water
  7. customThe solid was separated via filtration
  8. washwashed with water
  9. customair-dried
  10. customThe crude product was purified via flash column chromatography (eluent gradient: 5% to 30% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-86cce731f2f14898ae6c4fbfc5930a8a
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07589104B2

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