Cesium fluoride → HCID 70979015, Verbindung

HRID 1852278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852278
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[CH:4][N:3]=1.[F-:16].[Cs+]>CS(C)=O.O>[F:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 25953Cesium fluorideHCID 22250112HCID 22250112, Verbindung

Produkt 1

HCID 70979015HCID 70979015, VerbindungAusbeute 20,15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

To a solution of 1-chloro-4,6-dimethoxyisoquinoline (1.5 g, 6.71 mmol) in DMSO (15 ml) was added cesium fluoride (4 g, 26.8 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (280 mg, 20.15%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.99-7.97 (d, J=8 Hz, 1H), 7.44-7.39 (m, 2H), 7.27-7.11 (m, 1H), 4.03 (s, 3H), 3.97 (s, 3H); 19F NMR: δ ppm −79.32 (1F); MS: MS m/z 208.0 (M++1).

Aufarbeitung

  1. customThe reaction vessel (Pressure tube) was sealed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-493d0620c17d49eb8d04c557a303e765
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

Notizen zur Reaktion

Wird geladen…