Tetrahydrofuran → 5-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole

HRID 2190765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190765
[Cl:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]([OH:17])=[C:6]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]2[O:17][C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:8][C:6]=2[CH:7]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66879747N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide

Produkt 1

HCID 668802185-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazoleAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 0.55 g of N-[5-chloro-2-hydroxy-4-(trifluoromethyl)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.50 g of triphenylphosphine, 0.83 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resultant crystals were washed with methanol to give 0.11 g of 5-chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 78”).

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washthe resultant crystals were washed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-ee57314261c6462380182a9177543df3
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324387B2

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