Sodium Carbonate → 3,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 912587

Reaktionsgleichung

Reaktionsgleichung von HRID 912587
Br[C:2]1[C:3]([CH3:13])=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:5][C:6]=1[CH3:7].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([O:10][C:8]([C:4]1[NH:5][C:6]([CH3:7])=[C:2]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([F:26])([F:25])[F:14])[C:3]=1[CH3:13])=[O:9])[CH3:12]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 138486ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 27343872-(Trifluoromethyl)benzeneboronic acid

Produkt 1

HCID 598075413,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid ethyl esterAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate (2.4 g, 10 mmol) in DMF (25 mL) was added tetrakis(triphenylphosphine)palladium (2.3 g, 1 mmol). After stirring 15 min, the reaction mixture was charged with 2-(trifluoromethyl)-benzeneboronic acid (2.4 g, 12.5 mmol) and sodium carbonate (in 5 mL of water). The reaction mixture was heated to reflux overnight with stirring. After cooling, the reaction mixture was then diluted with water and extracted with DCM. The combined extracts were washed with water and dried over Na2SO4. Evaporation of solvent gave a crude material, which was purified by chromatography on silica gel column eluting with EtOAc-hexane (1:1) to give the title compound (1.5 g). MS (ES): 312 (MH+)

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. stirringwith stirring
  4. temperatureAfter cooling
  5. extractionextracted with DCM
  6. washThe combined extracts were washed with water
  7. dry with materialdried over Na2SO4
  8. customEvaporation of solvent
  9. customgave a crude material, which
  10. customwas purified by chromatography on silica gel column
  11. washeluting with EtOAc-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6bd8e29ff314a7ea2cc9c61e62a968d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026237B2

Verknüpfte Notizen

Wird geladen…