Cesium carbonate → (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one

HRID 70658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70658
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:33]1[CH:34]=[CH:35][C:36](/[C:41](/[C:49]2[CH:54]=[CH:53][C:52]([C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:51][CH:50]=2)=[CH:42]/[C@@H:43]2[NH:47][C:46](=[O:48])[CH2:45][CH2:44]2)=[N:37][C:38]=1[O:39][CH3:40]>O1CCOCC1.C(OCC)(=O)C.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:55]([C:52]1[CH:53]=[CH:54][C:49](/[C:41](/[C:36]2[CH:35]=[CH:34][C:33]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:38]([O:39][CH3:40])[N:37]=2)=[CH:42]\[C@@H:43]2[NH:47][C:46](=[O:48])[CH2:45][CH2:44]2)=[CH:50][CH:51]=1)([CH3:58])([CH3:57])[CH3:56]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 521585Tris(furan-2-yl)phosphaneHCID 58452636(5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

Produkt 1

HCID 67397019(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Phenylboronic acid (57 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), tri(2-furyl)phosphine (32 mg) and cesium carbonate (151 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42 (80 mg) in 1,4-dioxane (1.5 mL)-water (0.5 mL), and the mixture was stirred at an external temperature of 65° C. for three hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate 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→3:2) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one as an orange oil (81 mg).

Aufarbeitung

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

Quellen und Nachweise

ORD-Eintrag
ord-e796418d2b9f433caca48e576b24ad79
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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