Cesium carbonate → HCID 67400008, Verbindung

HRID 70700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70700
Br/[CH:2]=[C:3](/[C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([Cl:22])=[CH:16][CH:15]=1)\[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:10]([C:7]1[CH:8]=[CH:9][C:4](/[C:3](/[C:14]2[CH:15]=[CH:16][C:17]([Cl:22])=[C:18]([O:20][CH3:21])[N:19]=2)=[CH:2]\[N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:5][CH:6]=1)([CH3:13])([CH3:12])[CH3:11]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 634876Binap, (A+-)-HCID 58452310HCID 58452310, Verbindung

Produkt 1

HCID 67400008HCID 67400008, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A solution of 6-[(E)-2-bromo-1-(4-tert-butylphenyl)ethenyl]-3-chloro-2-methoxypyridine obtained in Reference Example 4-7 (109 mg), 2-pyrrolidone (73 mg), tris(dibenzylideneacetone)dipalladium(0) (11 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg) and cesium carbonate (329 mg) in toluene (3 mL) was stirred at an external temperature of 130° C. for four hours in a nitrogen atmosphere. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to give 1-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a yellow powder (82 mg, 75%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b51199273cbc416eb7e2ad12e5be6267
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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