Water → 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)-2-phenylacetamide

HRID 1473948

Reaktionsgleichung

[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:8][CH:9]=1.Br[CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23]([NH2:25])=[O:24].O>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7](=[N:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:8]([CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([NH2:25])=[O:24])[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Sodium hydride (0.040 g, 0.0017 mol) was suspended in N,N-dimethylformamide (15 mL) and was cooled at 0° C. N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide (compound a, 0.37 g, 0.0014 mol) was added and was stirred for 15 minutes. 2-Bromo-2-phenylacetamide h (0.3 g, 0.001 mol) was added then the reaction was warmed to room temperature and was stirred for 24 hours. The reaction was poured into water and extracted with ethyl acetate (3×50 mL) then dried then chromatographed on silica (50% ethyl acetate/hexanes) to give 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)-2-phenylacetamide (compound j) Rf 0.42, 50% ethyl acetate/hexanes; MS m/z 400 (M+H).

Aufarbeitung

temperaturethe reaction was warmed to room temperature
stirringwas stirred for 24 hours
extractionextracted with ethyl acetate (3×50 mL)
customthen dried
customthen chromatographed on silica (50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-ae06593cfdff4724afaca8e799f0d9cd
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09018208B2

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