Cesium carbonate → 1-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one

HRID 1431778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431778
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1([CH3:22])[CH2:20][NH:19][C:18](=[O:21])[CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:19]2[CH2:20][C:16]([CH3:22])([CH3:15])[CH2:17][C:18]2=[O:21])[C:11]=1[CH3:12]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6375934,4-Dimethyl-2-pyrrolidinoneHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

Produkt 1

HCID 596313401-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Prepared according to Procedure F using 2,4-dichloro-7-fluoro-3-methylquinoline (0.300 g, 1.304 mmol), 4,4-dimethyl-2-pyrrolidinone (0.162 mL, 1.434 mmol), cesium carbonate (0.600 g, 1.826 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.060 g, 0.065 mmol), XantPhos (0.113 g, 0.196 mmol), and dioxane (2.6 mL). Purification by column chromatography (silica; 0-20% EtOAc in hexanes) afforded 1-(4-chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one as a white amorphous solid. Mass Spectrum (ESI) m/e=307.0 (M+1).

Aufarbeitung

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-31775dea529341c0a1187062f74520f7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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