Cesium carbonate → HCID 58988073, Verbindung

HRID 79100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79100
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][C:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:14][C:15]1[C:20]([O:21][C:2]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:19][CH:18]=[CH:17][N:16]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 707192-Methylpyridin-3-olHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrile

Produkt 1

HCID 58988073HCID 58988073, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2-fluoro-4-(trifluoromethyl)benzonitrile (0.19 g, 1.0 mmol), 2-methylpyridin-3-ol (0.11 g, 1.0 mmol), and cesium carbonate (0.33 g, 1.0 mmol) in anhydrous DMF (5 mL) was heated at 50° C. for 16 h. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (0%-30% EtOAc-hexanes) to obtain 2-(2-methylpyridin-3-yloxy)-4-(trifluoromethyl)benzonitrile (0.26 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 8.50 (dd, J=4.7, 1.4 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.44 (dd, J=8.1, 0.7 Hz, 1H), 7.35 (dd, J=8.1, 1.4 Hz, 1H), 7.28-7.25 (m, 1H), 6.87 (s, 1H), 2.50 (s, 3H) ppm.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0%-30% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bcfe844ad5274be38422767fd75a52e4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841483B2

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