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2-Fluoro-5-iodobenzonitrile → 5-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]2-fluorobenzonitrile

HRID 1930524
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1930524
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:18][C:19]1[CH:26]=[CH:25][C:24](I)=[CH:23][C:20]=1[C:21]#[N:22]>C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12][N:11]([C:24]3[CH:25]=[CH:26][C:19]([F:18])=[C:20]([CH:23]=3)[C:21]#[N:22])[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1
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Komponenten

4

Edukt 2

HCID 27789282-Fluoro-5-iodobenzonitrileHCID 582188803-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

Produkt 1

HCID 582188895-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]2-fluorobenzonitrileAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (0.6 g) and 2-fluoro-5-iodobenzonitrile (0.57 g) was dissolved in toluene, which was then degassed 3 times. To the solution in toluene was added sodium tert-butoxide (0.20 g), Tris(dibenzylidene acetone)dipalladium chloroform complex (0.04 g) and Xantphos (0.07 g) under argon atmosphere, and the mixture was stirred at 80° C. for two hours. The mixture was cooled to room temperature and then diluted with ethyl acetate, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 5-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-fluorobenzonitrile (0.54 g). m.p. 184-186° C.

Aufarbeitung

  1. customwhich was then degassed 3 times
  2. additionTo the solution in toluene was added sodium tert-butoxide (0.20 g), Tris(dibenzylidene acetone)dipalladium chloroform complex (0.04 g) and Xantphos (0.07 g) under argon atmosphere
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with ethyl acetate, which
  5. washwas then washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter the drying agent was filtered off
  8. distillationthe solvent was distilled away under the reduced pressure
  9. customthe residue was then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-35b896f1465f405881ba9a15f694cda9
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188122B2

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