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

HRID 2266449ノート

反応式

HRID 2266449 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68773e53dee0441a9a37bb478604815a
出典データセット
uspto-grants-2010_12
特許番号
US07858640B2

反応ノート

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