3',5'-Di-O-acetyl-2'-deoxy-2'-fluoro-5-iodouridine synthesis

Yield:565226-18-8 96%

Reaction Conditions:

with Iodine monochloride in dichloromethane; for 5 h;Reflux;

Steps:

To a solution of 282 (1.65g, 5 mmol) in dichloromethane (50 ml) was added iodine monochloride (1.5 g, 9.24 mmol) and the mixture was heated under reflux for 5h. The reaction mixture was allowed to cool to room temperature and washed with 5% sodium bisulfite solution (100 ml) followed by sat. sodium bicarbonate solution ( 200 ml). Organic layer was dried and evaporated to give 2.2 g (96%) of 283. ¹U NMR (400 MHz, DMSO) δ 11.84 (s, IH), 8.18 (s, IH), 5.85 (dd, / = 22.1, 1.5, IH), 5.52 (ddd, / = 52.5, 5.2, 1.7, IH), 5.34 - 5.18 (m, IH), 4.41 - 4.24 (m, 2H), 4.18 (dd, / = 12.1, 5.2, IH), 2.07, 2.10 (2s , 6H). ¹⁹F-NMR: m, -200.75.

References:

WO2010/101951,2010,A1 Location in patent:Page/Page column 248