Sodium Acetate → HCID 68781569, compound

HRID 2266431Notes

Reaction equation

HRID 2266431 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:8]([CH3:27])=[N: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.[Cl-].[NH4+].[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: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]([CH3:27])=[N:9]2

Participants

8

Reactant 3

HCID 517045Sodium AcetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86631429HCID 86631429, compound

Product 1

HCID 68781569HCID 68781569, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trifluoromethanesulfonic acid 3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yl ester (0.39), 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (0.95 mL), sodium acetate (0.086 g), tris(dibenzylideneacetone) dipalladium (0) (0.080 g) and 1,1′-bis(diphenylphospino) ferrocene (0) (0.048 g) in N,N-dimethylformamide (3.0 mL) was heated by microwave irradiation at 120° C. for 10 minutes. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:1 by volume) gave title compound, 0.11 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel
  5. washeluting with a mixture of ethyl acetate and cyclohexane (1:1 by volume)

Sources & evidence

ORD record
ord-e5da96efa925471fbb246cd577aa972b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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