Cesium carbonate → 6-Fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-one

HRID 1930204

Reaktionsgleichung

Reaktionsgleichung von HRID 1930204
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[NH:17][CH:16]=[CH:15]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[N:17]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:16]=[CH:15]2

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 450908026-Fluoroisoquinolin-1(2H)-one

Produkt 1

HCID 598182606-Fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-oneAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

169 μL of p-methoxybenzylchloride (1.24 mmol, 1.1 eq) were added to a suspension of 200 mg of 6-fluoro-isoquinolinone (13) (1.13 mmol) and 368 mg of Cs2CO3 (1.36 mmol, 1.2 eq) in 3 mL of DMF. The mixture was stirred for 2 h and then poured on ice. The precipitate was filtered, washed with water and dried to yield 300 mg of the title compound. LCMS Method B, retention time 1.76 min, detected mass 284.14 [M+H]+

Aufarbeitung

  1. additionpoured on ice
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-69a7ed0ca77341ce88ef0eeaab37f2c0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188117B2

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