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

HRID 1913615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913615
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[I:20].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>[I:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:13]1[O:21][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=2[N:12]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66880065N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-iodoisonicotinamide

Produkt 1

HCID 668805972-(3-Iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazoleAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 1.81 g of N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-iodoisonicotinamide, 20 ml of tetrahydrofuran and 1.34 g of triphenylphosphine, 2.22 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 one hour. The reaction mixture was cooled to room temperature, and then the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.40 g of 2-(3-iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 29”).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a10d8006e1f245419c347e8ff91da38f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609705B2

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