Water → HCID 71060066, Verbindung

HRID 405137

Reaktionsgleichung

Reaktionsgleichung von HRID 405137
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:22])=[C:17](B(O)O)[CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:22])=[C:15]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH:14]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Produkt 1

HCID 71060066HCID 71060066, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl 5-bromopicolinate (5.0 g, 23.1 mmol), (5-chloro-2-methylphenyl)boronic acid (4.5 g, 26.6 mmol), Pd(dppf)Cl2 (1.9 g, 2.3 mmol), and K2CO3 (6.4 g, 46.3 mmol) were dissolved in 1,4-dioxane (100 mL) and water (25 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Quellen und Nachweise

ORD-Eintrag
ord-7b9e4725b0864c9fa9e388386c7b2497
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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