1,4-Dioxane → HCID 56992608, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-10-(benzyloxy)-2-(3-chloro-4-fluorobenzyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (1.00 g, 1.83 mmol), tributyl(1-ethoxyvinyl)tin (0.73 g, 2.01 mmol), and trans-dichlorobis(triphenylphosphine)palladium (II) (64 mg, 92 μmol) in dioxane (10 mL) was purged with nitrogen for 15 minutes. The reaction mixture was heated in a sealed tube at 100° C. overnight. The product mixture was filtered through a pad of Celite, and the filtrate concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of ethyl acetate in chloroform. Collecting and concentration of appropriate fractions provided the intermediate ethoxyvinyl ether as off white solid. A solution of the ethoxyvinyl ether (0.70 g, 1.30 mmol) in acetone at room temperature was treated with hydrochloric acid (2 mL, 1 M) and stirred at the same temperature for 30 minutes. The resultant solution was concentrated under vacuum to provide the title ketone.

Provenance & Evidence