Cesium fluoride → 5-(2-Fluoro-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-one

HRID 575812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575812
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([CH3:17])[C:3]1=[O:18].Br[C:20]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[F:30].[F-].[Cs+]>COCCOC.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:30][C:21]1[CH:20]=[CH:25][C:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:23][C:22]=1[C:6]1[CH:5]=[C:4]([CH3:17])[C:3](=[O:18])[N:2]([CH3:1])[CH:7]=1

Komponenten

7

Edukt 3

HCID 25953Cesium fluorideHCID 673870812-Bromo-1-fluoro-4-(methylsulfonyl)benzeneHCID 712703091,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one

Produkt 1

HCID 1180225965-(2-Fluoro-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-oneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 887MethanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (2.50 g, 10.0 mmol), 2-bromo-1-fluoro-4-methylsulfonylbenzene (2.54 g, 10.0 mmol), CsF (3.8 g, 25.0 mmol), Pd(dppf)Cl2 (0.73 g, 1.0 mmol) in DME (50 mL) and MeOH (25 ml) was stirred at 80° C. for 18 hrs under N2. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1) to give the title compound (1.8 g, 61%) as a red solid. LCMS: 295.9 (M+H)+

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1)

Quellen und Nachweise

ORD-Eintrag
ord-4cb4be705a7c4136a38a01f57919850b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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