Sodium Acetate → HCID 68784276, compound

HRID 2266434Notes

Reaction equation

HRID 2266434 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].[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].[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.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:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:21])=[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]([CH3:12])=[N:10]2

Participants

8

Reactant 3

HCID 517045Sodium AcetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86631430HCID 86631430, compound

Product 1

HCID 68784276HCID 68784276, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trifluoromethanesulfonic acid 8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl ester (0.24 g), 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (0.56 mL), sodium acetate (0.053 g), tris(dibenzylideneacetone) dipalladium (0) (0.024 g) and 1,1′-bis(diphenylphospino) ferrocene (0) (0.014 g) in N,N-dimethylformamide (2 mL) was heated by microwave irradiation at 120° C. for 10 minutes. The mixture was diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:9 to 1:6 by volume) to afford title compound as a pink solid, 0.12 g.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel
  5. washeluting with a mixture of ethyl acetate and cyclohexane (1:9 to 1:6 by volume)

Sources & evidence

ORD record
ord-66f17faa68c04e6e9b3229d47517a29f
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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