Tetrahydrofuran → 2-(3-Bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 884848

Reaktionsgleichung

Reaktionsgleichung von HRID 884848
[Br:1][C:2]1[CH:21]=[N:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[OH:17])=O.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>[Br:1][C:2]1[CH:21]=[N:20][CH:19]=[CH:18][C:3]=1[C:4]1[O:17][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[N:6]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 668798803-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

Produkt 1

HCID 668809172-(3-Bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazoleAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 4 ml of tetrahydrofuran and 0.25 g of triphenylphosphine, 0.42 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred while heating at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.24 g of 2-(3-bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 27”).

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b05badc6d13144ecb3eb9b1b6f6f9511
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242133B2

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