Sodium hydride → HCID 178470053, Verbindung

HRID 1497089Notizen

Reaktionsgleichung

[H-].[Na+].[CH2:3]([O:5][C:6](=[O:27])[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])=[O:9])[CH3:4]>CS(C)=O.C(OCC)(=O)C>[CH2:3]([O:5][C:6]([C:7]1[C:8]([OH:9])=[N:10][C:11]2[C:12]([C:18]=1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[O:27])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of sodium hydride (60%; 32 mg, 0.8 mmol) in DMSO (3 ml) was added a solution of N-[4-chloro-2-(2-chloro-phenylethynyl)-phenyl]-malonamic acid ethyl ester (200 mg, 0.532 mmol) in DMSO (2 ml) under nitrogen at 25° C., and the reaction mixture was stirred for 2 h at 80° C. The reaction mixture was diluted with ethyl acetate (15 ml), and the organic layer was washed with brine (3×10 ml), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (20% EtOAc in hexane) to afford 6-chloro-4-(2-chloro-benzyl)-2-hydroxy-quinoline-3-carboxylic acid ethyl ester (63 mg, 32%) as an off white solid. LC-MS (ESI): 376 (M+H)+.

Aufarbeitung

washthe organic layer was washed with brine (3×10 ml)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a crude residue which
customwas purified by flash column chromatography (20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-9a15032c9c704d72b46ef2cd469387ee
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09199938B2

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