Potassium Phosphate, Tribasic → [4-(3-Chloropyrazin-2-yl)phenyl]acetic acid

HRID 474142

Reaktionsgleichung

Reaktionsgleichung von HRID 474142
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)O1.[Cl:20][C:21]1[C:26](Cl)=[N:25][CH:24]=[CH:23][N:22]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:20][C:21]1[C:26]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=2)=[N:25][CH:24]=[CH:23][N:22]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 785752,3-DichloropyrazineHCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic Acid

Produkt 1

HCID 59535937[4-(3-Chloropyrazin-2-yl)phenyl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 0.10 g (0.38 mmol) [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid in 1.2 ml of dioxane was added 0.17 g (1.15 mmol) of 2,3-dichloropyrazine, 2.57 mg (0.009 mmol) of tricyclohexylphosphine, 3.5 mg (0.004 mmol) of Pd2(dba)3, and 0.51 ml (1.27 M, 0.65 mmol) of aqueous potassium phosphate solution. The resulting suspension was degassed for 10 minutes. After 30 min in the microwave at 100° C., the reaction mixture was cooled, acidified with 1N HCl, extracted with ethyl acetate, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afford crude [4-(3-chloropyrazin-2-yl)phenyl]acetic acid. ES-MS M+1=249.1.

Aufarbeitung

  1. customThe resulting suspension was degassed for 10 minutes
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1df42e582d8249e392fc58df6c37ccc4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637513B2

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