Reaktion #1155207

Reaktionsgleichung

3-butyn-1-ol

N-(4-chlorobenzyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

→

title compound

N-(4-Chlorobenzyl)-8-(4-hydroxy-1-butynyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Lösungsmittel

—

Hexanes

diethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe resulting solid is filtered
2. 2
   Sonstigedried
3. 3
   workup.DISSOLUTIONThe solid is dissolved in CH2Cl2/MeOH
4. 4
   SonstigePurification by chromatography (eluent CH2Cl2 (1 L), 1.5% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (2 L), 3% MeOH:CH2Cl2 (1 L))

Vorschrift

A solution of N-(4-chlorobenzyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.22 g) from Preparation No. 48, copper iodide (0.029 g), bis(triphenylphosphine)palladium(II) chloride (0.013 g), and 3-butyn-1-ol (0.040 mL) in diethylamine (15 mL) is stirred at room temperature for 18 h. Hexanes are added to the reaction mixture and the resulting solid is filtered and dried. The solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1 L), 1.5% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (2 L), 3% MeOH:CH2Cl2 (1 L)) affords the title compound as a light yellow solid (0.16 g).

Quelle