Potassium Carbonate → Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

HRID 405237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405237
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH:28]=[O:29])=[C:23](B(O)O)[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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:18][C:19]1[CH:24]=[CH:23][C:22]([CH:28]=[O:29])=[C:21]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[N:6][CH:7]=2)[CH:20]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 38069525-Chloro-2-formylphenylboronic acidHCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

Produkt 1

HCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ethyl 3-(5-bromopicolinamido)propanoate (2.2 g, 7.3 mmol), (5-chloro-2-formylphenyl)boronic acid (1.4 g, 7.7 mmol), Pd(dppf)Cl2 (810 mg, 1.1 mmol), and K2CO3 (2.3 g, 16.9 mmol) and PdCl2(dppf) were dissolved in wet DMF (10 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. temperatureAfter 16 h the resulting mixture was cooled to room temperature
  2. filtrationfiltered through CELITE
  3. additionthe filtrate was diluted with EtOAc
  4. washwashed with water and sat. aqueous NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28d523e14b8342a2895a55997efc6abd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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