Reaktion #1155206

Reaktionsgleichung

propargyl alcohol

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

Dichloromethane

→

title compound

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

Lösungsmittel

diethylamine

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added to the reaction mixture
2. 2
   FiltrationThe resulting solid is filtered
3. 3
   Waschenwashed thoroughly with hexanes
4. 4
   Sonstigedried
5. 5
   workup.DISSOLUTIONThe solid is dissolved in CH2Cl2/MeOH
6. 6
   SonstigePurification by chromatography (eluent CH2Cl2 (1 L), 0.5% MeOH:CH2Cl2 (1 L), 1% MeOH:CH2Cl2 (1 L), 1.5% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L), 3% MeOH:CH2Cl2 (1 L))

Vorschrift

A solution of N-(4-chlorobenzyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.21 g) from Preparation No. 48, copper iodide (0.029 g), bis(triphenylphosphine)palladium(II) chloride (0.012 g), and propargyl alcohol (0.035 mL) in diethylamine (15 mL) is stirred at room temperature for 18 h. Dichloromethane followed by hexanes is added to the reaction mixture. The resulting solid is filtered, washed thoroughly with hexanes, and dried. The solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1 L), 0.5% MeOH:CH2Cl2 (1 L), 1% MeOH:CH2Cl2 (1 L), 1.5% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L), 3% MeOH:CH2Cl2 (1 L)) affords the title compound as a yellow solid (0.13 g).

Quelle