Water → HCID 86674254, Verbindung

HRID 405168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405168
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=2)O1.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]>[F:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=2)[CH:9]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 467386632-Methoxycarbonyl-5-pyridineboronic acid, pinacol ester

Produkt 1

HCID 86674254HCID 86674254, 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

2-bromo-4-fluorobenzaldehyde (800 mg, 3.9 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (1.2 g, 4.7 mmol), Pd(dppf)Cl2 (433 mg, 0.6 mmol), and K2CO3 (1.1 g, 7.9 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 65° C. After 1.5 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-f7a9f8b8283146e1bcbf90774b624ee6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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