Potassium Carbonate → 6-(4-Cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 406417

Reaktionsgleichung

Reaktionsgleichung von HRID 406417
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[CH:7]=1.[CH:15]1([C:18]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:15]1([C:18]2[CH:23]=[CH:22][C:21]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=4)[CH:7]=3)=[CH:20][CH:19]=2)[CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 28494284-Cyclopropylbenzeneboronic acidHCID 581189066-Bromo-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-a)pyridine

Produkt 1

HCID 581189736-(4-Cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of 6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (50 mg, 0.19 mmol), 4-cyclopropyl phenylboronic acid (34 mg, 0.21 mmol), dppf(Pd)Cl2 (6.9 mg, 0.094 mmol), potassium carbonate (52 mg, 0.62 mmol) in degassed toluene (1 mL), degassed water (0.5 mL) and degassed ethanol (0.5 mL) was heated at 90° C. for 1 hour. The layers are separated, the organic layer was concentrated and the residue was purified by column chromatography to provide 6-(4-cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine as a white powder.

Aufarbeitung

  1. customdegassed water (0.5 mL)
  2. customdegassed ethanol (0.5 mL)
  3. customThe layers are separated
  4. concentrationthe organic layer was concentrated
  5. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-919e50792a8544b68a08805ddfb0ac2f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754103B2

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