Triethylamine → HCID 178418902, Verbindung

HRID 7805

Reaktionsgleichung

[NH2:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.CO>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=2)[C:3]([OH:9])=[N:4][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 3-amino-5-bromopyridin-2-ol from Step C (1.5 g, 7.9 mol) and triethylamine (1.64 mL, 11.9 mol) in tetrahydrofuran (15.8 mL) at 0 C was added dropwise 4-trifluoromethylbenzoyl chloride (1.2 mL, 7.9 mol). The reaction mixture was stirred at 0° C. for 1 h and warmed to room temperature for 15 h. Potassium carbonate (1.64 g, 11.9 mol) and methanol (15.8 mL) were added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated ammonium chloride solution and brine. The separated organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 1.72 g (60%) of the title compound.

Aufarbeitung

temperaturewarmed to room temperature for 15 h
stirringthe reaction mixture was stirred at room temperature for 6 h
washwashed with saturated ammonium chloride solution and brine
dry with materialThe separated organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-398716f2fe394a7f9a626f6e1dd67830
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087622B2

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