Sodium Acetate → [7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic Acid Methyl Ester

HRID 2266449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266449
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:21])=[C:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[C:8]([CH3:12])=[N:9]2)=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.ClC1C=C(OS(C(F)(F)F)(=O)=O)C=C2C=1C(C)=C(CC1C=CC(Cl)=CC=1)C(C)=N2.C([Si]([O:66][C:67]([O:69][CH3:70])=[CH2:68])(C)C)(C)(C)C.C([O-])(=O)C.[Na+]>CN(C)C=O.C(OCC)(=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:70][O:69][C:67](=[O:66])[CH2:68][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[C:6]([CH3:21])=[C:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]([CH3:12])=[N:9]2

Komponenten

9

Edukt 4

HCID 517045Sodium AcetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86631431Trifluoromethanesulfonic Acid 7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl EsterHCID 86631432Trifluoromethanesulfonic acid 5-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-7-yl ester

Produkt 1

HCID 68782352[7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl]acetic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl ester and trifluoromethanesulfonic acid 5-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-7-yl ester (0.86 g), tert-butyl-(1-methoxyvinyloxy)-dimethyl silane (2.0 mL), sodium acetate (0.18 g), bis(dibenzylideneacetone) palladium (0.05 g) and 1,1′-bis(diphenylphospino) ferrocene (0) (0.05 g) in N,N-dimethylformamide (11.0 mL) was heated by microwave irradiation at 120° C. for 15 minutes. The mixture was diluted with ethyl acetate and this solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution and then dried over-magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane, ethyl acetate and pentane (4:0:1 to 1:0:0 to 50:1:0 to 25:1:0 to 12.5:1:0 by volume) gave title compound as a honey coloured gum, 0.25 g.

Aufarbeitung

  1. washthis solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over-magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane, ethyl acetate and pentane (4:0:1 to 1:0:0 to 50:1:0 to 25:1:0 to 12.5:1:0 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-68773e53dee0441a9a37bb478604815a
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858640B2

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