Dimethylformamide → 2-[3-(2,2,2-Trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazole

HRID 1913622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913622
[H-].[Na+].CN(C=O)C.[F:8][C:9]([F:13])([F:12])[CH2:10][OH:11].F[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=2[N:25]=1>O>[F:8][C:9]([F:13])([F:12])[CH2:10][O:11][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=2[N:25]=1

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Produkt 1

HCID 866510412-[3-(2,2,2-Trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazoleAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.06 g of 55% sodium hydride (in oil) and 2 ml of DMF was stirred at room temperature. To the mixture, a mixture solution of 0.13 g of 2,2,2-trifluoroethanol and 0.5 ml of DMF was added. The mixture solution was stirred at the same temperature for 15 minutes, and then 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole was stirred at room temperature for one hour. Water was added to the reaction mixture, which followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.27 g of 2-[3-(2,2,2-trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 39”).

Aufarbeitung

  1. stirringThe mixture solution was stirred at the same temperature for 15 minutes
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-654ef87aac1a48368288144d0d8d9aab
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609705B2

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