2,6-Dichloro-4-(trifluoromethyl)benzaldehyde → Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405251
Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:23]2[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:30])=[N:27][CH:28]=2)O1>O1CCOCC1.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:14][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:30])=[N:27][CH:28]=2)[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=1

Komponenten

6

Edukt 2

HCID 147939142,6-Dichloro-4-(trifluoromethyl)benzaldehydeHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate

Produkt 1

HCID 86674266Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2,6-Dichloro-4-(trifluoromethyl)benzaldehyde (3.2 g, 13.2 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (1.5 g, 4.4 mmol), Pd(dppf)Cl2 (320 mg, 0.4 mmol) and K3Pa4hydrate (3.0 g, 13.2 mmol) were dissolved in 1,4-dioxane (200 mL) and the resulting mixture was heated to 90° C. After 10 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-50bc7f0a6f3648f29cc479efd9b6d6c0
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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