Sodium Carbonate → 1-((4'-Butoxy(1,1'-biphenyl)-4-yl)thio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone

HRID 1978025

Reaktionsgleichung

Reaktionsgleichung von HRID 1978025
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]2=[O:20])=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]3[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]3=[O:20])=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 38363104-Butoxyphenylboronic AcidHCID 217002621-(4-Bromophenylthio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone

Produkt 1

HCID 110375531-((4'-Butoxy(1,1'-biphenyl)-4-yl)thio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanoneAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of Example 46A (700 mg, 1.89 mmol) in DME (20 mL) at room temperature was treated with 4-n-butoxybenzeneboronic acid (549 mg, 2.83 mmol), tetrakis-(triphenylphosphine)-palladium (218 mg, 0.189 mmol) and 1M sodium carbonate (3.54 mL, 3.54 mmol), the reaction vessel was sealed and heated at 90° C. for 6 hours, diluted with ethyl acetate, washed with sequentially saturated ammonium chloride solution, water and brine, dried (Na2SO4), filtered, concentrated and purified on silica gel with 30 to 50% ethyl acetate/dichloromethane to provide 650 mg (78%) of the desired product as a yellow solid.

Aufarbeitung

  1. customthe reaction vessel was sealed
  2. washwashed with sequentially saturated ammonium chloride solution, water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel with 30 to 50% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-89b45d9ae1264a8bb277584400006a80
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235786B1

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