Sodium Bicarbonate → HCID 22316823, Verbindung

HRID 497188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497188
[CH3:1][C:2]1[O:3][C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=2)[N:6]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[O:3][C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:9][CH:8]=2)[N:6]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 223167672-Methyl-5-[4-(methylsulfonyl)phenyl]-4-(4-bromophenyl)-oxazole

Produkt 1

HCID 22316823HCID 22316823, VerbindungAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methyl-5-[4-(methylsulfonyl)phenyl]-4-(4-bromophenyl)-oxazole (0.314 g, 0.8 mmol) in DME (10 mL) was added thiophene-2-boronic acid (0.123 g, 0.96 mmol), bis(triphenylphosphine)palladium(II)chloride (0.064 g, 0.09 mmol) and saturated NaHCO3 solution (3.2 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 4.5 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3/2). The resulting solid was recrystallized from ethyl acetate/hexane to give the title compound (0.225 g, 71.2% yield).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4.5 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additionthe filtrate was poured into water
  5. extractionthe whole was extracted with ethyl acetate (10 mL×3)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with hexane/ethyl acetate (3/2)
  11. customThe resulting solid was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-047a4a69826f480ba9618d6d2ce584bf
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949536B2

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