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

HRID 2266449Notes

Reaction equation

HRID 2266449 reaction equation
[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

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-68773e53dee0441a9a37bb478604815a
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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