Sodium Carbonate → 6-(3-Fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1846938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846938
[F:1][C:2]([F:16])([F:15])[C:3]1[N:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[C:20]([F:29])[CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[F:29][C:20]1[CH:19]=[C:18]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:16])([F:15])[F:1])=[N:4][N:5]=3)[CH:8]=2)[CH:23]=[CH:22][C:21]=1[O:24][C:25]([F:26])([F:27])[F:28]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27822174-Bromo-2-fluoro-1-(trifluoromethoxy)benzeneHCID 581189153-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid

Produkt 1

HCID 866502296-(3-Fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid (56.2 mg, 0.217 mmol), 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene (50.0 mg, 0.217 mmol, 1.0 equiv.) and Pd(PPh3)4 (12.6 mg, 0.0109 mmol, 0.05 equiv.) was placed in a 50 mL round bottomed flask under a nitrogen atmosphere. To the flask were added 2M-Na2CO3 (1.0 mL, 2.0 mmol) and DMF (4 mL) subsequently at ambient temperature. The mixture was heated at 110° C. for 1 hours. The mixture was filtered through Celite (3 g) and the Celite was washed with EtOAc (70 mL). The organic layer was washed with brine (30 mL) and dried with Na2SO4. The solvent was removed under a reduced pressure. Obtained crude mixture was purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:3 to 1:1, Rf=0.3 with EtOAc/hexane=1:1) to give 6-(3-fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine as colorless crystals

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite (3 g)
  2. washthe Celite was washed with EtOAc (70 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under a reduced pressure
  6. customObtained crude mixture
  7. customwas purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:3 to 1:1, Rf=0.3 with EtOAc/hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7572b9b7f68c4feb9f92da459540676e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952034B2

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