To a stirred solution of 350 g (10.1 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 50 ml dioxane were added 5.63 g (15.1 mmol) tributyl-(3,6-dihydro-2H-pyran-4-yl)-stannane, 173 mg (0.30 mmol) bis(dibenzylideneacetone)palladium(0), 374 mg (1.61 mmol) tri(2-furyl)phospine. The mixture was heated at 100° C. for 22 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (2/98 methanol/dichloromethane then 5/95 methanol/dichloromethane) followed by trituration in dichloromethane afforded 1.30 g (42%) [7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester as a white solid. ES-MS m/e (%): 305 (M+H+, 100).
