Ethanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester

HRID 1505270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505270
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)=[CH:4][C:3]=1[CH3:25].[C:26]([O-:29])(=[O:28])C.[Na+].[C]=O.[CH2:33](O)[CH3:34]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:33]([O:29][C:26](=[O:28])[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:14])([F:16])[F:15])[CH:10]=[N:9]2)=[CH:4][C:3]=1[CH3:25])[CH3:34]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 866589832-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrroleHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 672174284-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrole (Example 10.4) (7.0 g) in a mixture of ethanol (60 ml) and dimethylformamide (20 ml), was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (“PdCl2(dppf)”) (0.8 g) and sodium acetate (1.4 g) at ambient temperature. The reaction mixture was stirred in a pressure reactor in an atmosphere of carbon monoxide (6 bar) at 85° C. for 16 hours. The reaction mixture was cooled to ambient temperature, the ethanol was evaporated and aqueous sodium hydrogen carbonate (saturated) (200 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: 0-4% v/v methanol in dichloromethane) to give 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester (2.8 g). 1H-NMR (CDCl3, 400 MHz): 8.04-7.06 (m, 7H), 5.46-5.06 (m, 1H), 4.35 (m, 2H), 3.27-3.79 (m, 1H), 2.59 (m, 3H), 2.38-2.10 (m, 1H), 1.39 (m, 3H) ppm.

Aufarbeitung

  1. customthe ethanol was evaporated
  2. additionaqueous sodium hydrogen carbonate (saturated) (200 ml) and ethyl acetate (250 ml) were added
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent: 0-4% v/v methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-7450e8e2aa7947909013dd21ab189a06
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216973B2

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