Cesium carbonate → 1-Chloro-4-cyclopropoxy-7-fluoroisoquinoline

HRID 1852219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852219
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:20]1(Br)[CH2:22][CH2:21]1>CN(C=O)C.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13][CH:20]2[CH2:22][CH2:21]2)=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 78037BromocyclopropaneHCID 717427161-Chloro-7-fluoroisoquinolin-4-OL

Produkt 1

HCID 717427171-Chloro-4-cyclopropoxy-7-fluoroisoquinolineAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

To a solution of 1-chloro-7-fluoroisoquinolin-4-ol (1 g, 5.06 mmol) in DMF (5 mL) was added Cs2CO3 (4.95 g, 15.18 mmol) followed by cyclopropyl bromide (1.2 mL, 15.18 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 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 (0.24 g, 20%) as a yellow solid.

Aufarbeitung

  1. customThe reaction vessel (Pressure tube) was sealed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe 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-90e4ba75d2634f249bc70efed15c7a96
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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