1,2-Dimethoxyethane → 5-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde

HRID 1012487

Reaktionsgleichung

Reaktionsgleichung von HRID 1012487
Br[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH3:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>O>[CH3:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 578319835-bromo-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 866309885-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehydeAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

5-Bromo-1H-pyrrole-3-carbaldehyde (174 mg), [2-(methylthio)phenyl]boronic acid (202 mg) and sodium carbonate (254 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (58 mg) was added, and the mixture was further degassed and stirred at 105° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→4:1) to give the title compound as pale-yellow crystals (yield 150 mg, 69%).

Aufarbeitung

  1. customthe mixture was sufficiently degassed under a nitrogen atmosphere
  2. additionTetrakis(triphenylphosphine)palladium (58 mg) was added
  3. customthe mixture was further degassed
  4. temperatureto cool to room temperature
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c2ddabc938834bfcb92bd3419c3592f5
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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