Sodium Acetate → HCID 68605729, compound

HRID 2266425Notes

Reaction equation

HRID 2266425 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:8](=[O:27])[NH:9][C:10]3[C:15]([C:16]=2[CH3:17])=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=[C:12]([CH3:26])[CH:11]=3)=[CH:4][CH:3]=1.[Si]([O:37][C:38]([O:40][CH3:41])=[CH2:39])(C(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]>[CH3:41][O:40][C:38](=[O:37])[CH2:39][C:14]1[CH:13]=[C:12]([CH3:26])[CH:11]=[C:10]2[C:15]=1[C:16]([CH3:17])=[C:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:29][CH:28]=1)[C:8](=[O:27])[NH:9]2

Participants

8

Reactant 3

HCID 517045Sodium AcetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86631428HCID 86631428, compound

Product 1

HCID 68605729HCID 68605729, compound

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 3-(4-chlorobenzyl)-4,7-dimethyl-2-oxo-1,2-dihydroquinolin-5-yl ester (1.1 g), 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (2.7 mL), sodium acetate (0.25 g), bis(dibenzylideneacetone) palladium (0.07 g) and 1,1′-bis(diphenylphospino) ferrocene (0) (0.07 g) in N,N-dimethylformamide (15.0 mL) was heated by microwave irradiation at 120° C. for 15 minutes. The mixture was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, water 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 ethyl acetate and dichloromethane (0:1 to 1:3 by volume) gave title compound as a pale orange oil, 1.75 g.

Workup

  1. washwashed with saturated aqueous ammonium chloride solution, water 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 ethyl acetate and dichloromethane (0:1 to 1:3 by volume)

Sources & evidence

ORD record
ord-2ffc7a4d67704d2588460774436c9a6f
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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