Dimethylformamide → n-[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-difluoromethoxy-phenyl)-n-methyl-isobutyramide

HRID 547758

Reaktionsgleichung

Reaktionsgleichung von HRID 547758
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1.CN(C)C=O.Cl[C:36]([F:43])([F:42])C(OCC)=O>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]2[CH:18]=[C:17]([O:19][CH:36]([F:43])[F:42])[CH:16]=[C:15]([Cl:20])[CH:14]=2)([CH3:11])[CH3:12])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 86597668HCID 86597668, Verbindung

Produkt 1

HCID 87304771n-[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-difluoromethoxy-phenyl)-n-methyl-isobutyramideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 0.700 g (1.56 mmol) N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3-chloro-5-hydroxy-phenyl)-N-methyl-isobutyramide in 10 ml N,N-Dimethylformamide 0.215 g (1.56 mmol) K2CO3 and 0.2 ml (1.56 mmol) ethyl chlordifluoroacetate was added and the resulting suspension heated at 65° C. for 15 h. After cooling to ambient temperature, the reaction mixture was poured into 75 ml water and extracted three times with 80 ml CH2Cl2. The combined organic solvents were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 4:1) to give 0.38 g (49%) of the title compound as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted three times with 80 ml CH2Cl2
  3. dry with materialThe combined organic solvents were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6649c87f912c42efa9ad52606b63f7a8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939533B2

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