Silicon tetrachloride → 2-Fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

HRID 77790

Reaktionsgleichung

Reaktionsgleichung von HRID 77790
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[C:5]=1[F:23].[N-:25]=[N+:26]=[N-:27].[Na+].[Si](Cl)(Cl)(Cl)Cl>C(#N)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[N:27][N:26]=[N:25]2)[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[C:5]=1[F:23]

Komponenten

5

Edukt 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 666642332-Fluoro-5-isobutyrylamino-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Produkt 1

HCID 577498132-Fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl esterAusbeute 90.822,203 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Fluoro-5-isobutyrylamino-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (690 mg, 1.89 mmol), NaN3 (1.1 g, 17 mmol) and SiCl4 (964 mg, 5.67 mmol) were added 20 mL acetonitrile, and the reaction mixture refluxed for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in saturated aqueous NaHCO3, and the resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 610 g (83%) of 2-fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester.

Aufarbeitung

  1. temperaturethe reaction mixture refluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in saturated aqueous NaHCO3
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d302cd83f20244e2983731f1bd9a4106
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841336B2

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