Ethyl Acetate → N-{5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl}-2,6-difluorobenzamide

HRID 1896193

Reaktionsgleichung

Reaktionsgleichung von HRID 1896193
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1B(O)O.Br[C:16]1[N:17]=[CH:18][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[F:31])=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>[Pd].O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:16]1[N:17]=[CH:18][C:19]([NH:22][C:23](=[O:32])[C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[F:31])=[N:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27826702-Chloro-5-(trifluoromethyl)phenylboronic acidHCID 53415197N-(5-Bromopyrazin-2-YL)-2,6-difluorobenzamide

Produkt 1

HCID 11546102N-{5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl}-2,6-difluorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-5-trifluoromethyl-benzeneboronic acid (a, 5 mmol), N-(5-bromo-pyrazin-2-yl)-2,6-difluoro-benzamide (b, 5 mmol), palladium catalyst (0.30 mmol), potassium carbonate (1 g) in dry 1,4-dioxane (20 mL) was heated at 100° C. for 24 h. The mixture was taken up with ethyl acetate (EtOAc) (100 mL), washed with water (2×100 mL) and dried over Na2SO4. The oil obtained on concentration was purified by flash chromatography followed by recrystallization to give Compound 1 as a yellowish solid (0.19 g).

Aufarbeitung

  1. washwashed with water (2×100 mL)
  2. dry with materialdried over Na2SO4
  3. customThe oil obtained on concentration
  4. customwas purified by flash chromatography
  5. customfollowed by recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-80ab8f0babcb4f2c8f71c579f7e1d452
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518950B2

Verknüpfte Notizen

Wird geladen…