Isobutylene → HCID 70496137, Verbindung

HRID 2408137Notizen

Reaktionsgleichung

[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[CH2:26]=[C:27]([CH3:29])[CH3:28].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:19]=[C:20]([CH:21]2[CH2:26][C:27]([CH3:29])([CH3:28])[C:12]3[C:13](=[CH:14][CH:15]=[C:10]([S:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)(=[O:9])=[O:8])[CH:11]=3)[NH:16]2)[CH:23]=[CH:24][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 4-(morpholine-4-sulfonyl)-phenylamine (3 g, 12.4 mmol) and 3-bromo-benzaldehyde (2.52 g, 13.6 mmol) in acetonitrile (150 mL) were added isobutene (2.7 mL, 37.2 mmoll) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (1.54 g, 2.5 mmol). The resulting mixture was stirred at 80° C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4-dimethyl-6-(morpholine-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline (2.7 g, 47.4%) as a light yellow solid: MS (ESI) M+1=465.0 & 467.0.

Aufarbeitung

washwashed with water (100 mL×2) and brine (100 mL×2)
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed in vacuo
customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag: ord-7cd534a5f6a748dca3d5ad0d9fb35dd2
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08809369B2

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