1,4-Dioxane → HCID 178522856, compound

Participants

Reaction Steps

A deoxygenated mixture of 0.75 g of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 40, 0.75 g of 2-(tributylstannyl)thiophene, 60 mg of bis(triphenylphosphine)palladium(II)dichloride, 7.5 mL of dioxane and 2.5 mL of DMPU is stirred for 2 h at 100° C. The cooled mixture is diluted with 20 mL of hexanes and 60 mL of distilled water. The mixture is stirred for 5 minutes and then filtered. The solid is washed with two 50 mL portions of distilled water and then with two 25 mL portions of methyl t-butyl ether. It is then dissolved in 20 mL of refluxing acetic acid, treated with 2 g of activated carbon and filtered through celite. The volume of the filtrate is reduced to 10 mL and the hot solution diluted with 10 mL of distilled water. Upon cooling, 0.3 g of the title compound precipitates and is collected by filtration.

Provenance & Evidence