Tris(furan-2-yl)phosphane → [7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl ester

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Reaction Conditions

Reaction Steps

To a stirred solution of 5.0 g (13.2 mmol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid ethyl ester in 60 ml dioxane were added 6.94 g (18.5 mmol) tributyl-(5,6-dihydro-[1,4]dioxin-2-yl)-stannane, 456 mg (0.79 mmol) bis(dibenzylideneacetone)palladium and 491 mg (2.12 mmol) trifurylphosphine. The mixture was heated at 100° C. for 3 h, then cooled to room temperature and concentrated in vacuo. Flash chromatography (5/95 acetone/dichloromethane) afforded 4.00 g (90%) [7-(5,6-dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl ester as a light yellow foam. ES-MS m/e (%): 337 (M+H+, 100).

Provenance & Evidence