Potassium Carbonate → 3-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1846952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846952
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([Cl:14])([F:13])[F:12])=[N:9][N:10]=2)[CH:7]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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:11]([F:13])([F:12])[C:8]1[N:6]2[CH:7]=[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[F:28])=[CH:23][CH:22]=3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 581189096-Bromo-3-(chlorodifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

Produkt 1

HCID 581189423-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Bromo-3-(chloro-difluoro-methyl)-[1,2,4]triazolo[4,3-a]pyridine (2.76 g, 9.8 mmol), 4-trifluoromethoxyphenyl boronic acid (2.5 g, 12.1 mmol), dppfPdCl2 (1,1′-bis(diphenylphosphino)ferrocene palladium dichloride)(350 mg, 0.5 mmol), and potassium carbonate (2.76 g, 20 mmol) were suspended in degassed toluene (20 mL), degassed isopropanol (10 mL) and degassed water (10 mL) under an atmosphere of nitrogen. The reaction mixture was heated at 70° C. for 1 hour before being cooled to room temperature. The aqueous phase was discarded and the organic phase was concentrated and purified by flash chromatography (rf=0.5 in 1:1 hexanes/ethyl acetate) to give 3-(chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine as a pale orange powder.

Aufarbeitung

  1. customdegassed isopropanol (10 mL)
  2. customdegassed water (10 mL) under an atmosphere of nitrogen
  3. temperaturebefore being cooled to room temperature
  4. concentrationthe organic phase was concentrated
  5. custompurified by flash chromatography (rf=0.5 in 1:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-183bd5da2ae84eb0822c989155de59bd
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952034B2

Notizen zur Reaktion

Wird geladen…