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

HRID 2094406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2094406
[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-87b439adc1da430d81d7ab67b699be7c
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445522B2

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