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Cesium carbonate → 4-Benzyloxy-3-[(4-(2-methoxycarbonylphenyl)thio-3,5,6-trifluoropyridin-2-yl)oxy]benzonitrile

HRID 1636304
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Reaktionsgleichung

Reaktionsgleichung von HRID 1636304
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[N:15]=[C:14](F)[C:13]=1[F:21])=[O:4].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=1[OH:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=1[O:38][C:14]1[C:13]([F:21])=[C:12]([S:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[C:17]([F:18])=[C:16]([F:19])[N:15]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 14797Potassium HydroxideHCID 154534494-(2-Methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridineHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrile

Produkt 1

HCID 154534524-Benzyloxy-3-[(4-(2-methoxycarbonylphenyl)thio-3,5,6-trifluoropyridin-2-yl)oxy]benzonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridine (1.8 g, 5.7 mmol) in DMF (25 mL) was added 2-benzyloxy-5-cyanophenol (1.3 g, 5.8 mmol) and cesium carbonate (2.2 g, 6.8 mmol). The resultant mixture was stirred at 40° C. for 12 hours. The mixture was then cooled to ambient temperature and poured into 100 mL of 0.5 M aqueous KOH solution and 100 mL of ethyl acetate. The aqueous layer was separated and extracted twice further with 100 mL portions of ethyl acetate. The combined organic extracts were washed with 0.5 M aqueous KOH solution (200 mL), then brine (200 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford a yellow solid. Recrystallization from ethyl acetate/hexanes afforded 2.4 g (82% yield) of 4-benzyloxy-3-[(4-(2-methoxycarbonylphenyl)thio-3,5,6-trifluoropyridin-2-yl)oxy]benzonitrile, a compound of formula (E), as a white, crystalline solid: NMR (CDCl3) 8.0 (m, 1), 7.5 (m, 2), 7.4-7.1 (m, 8), 6.8 (br t, 1), 5.2 (s, 2), 4.0 (s, 3) ppm.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted twice further with 100 mL portions of ethyl acetate
  3. washThe combined organic extracts were washed with 0.5 M aqueous KOH solution (200 mL)
  4. dry with materialbrine (200 mL), dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow solid
  8. customRecrystallization from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-42431612410c455aae72e91381fe1318
Quelldatensatz
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06034084

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