1,4-Dioxane → HCID 56992608, compound

Temperature

100 °C

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.

1. customwas purged with nitrogen for 15 minutes
2. filtrationThe product mixture was filtered through a pad of Celite
3. concentrationthe filtrate concentrated under vacuum
4. additionThe residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of ethyl acetate in chloroform
5. customCollecting

ORD record

ord-0c39ad3aa32a46d990a20aeec17f1df7

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538112B2