Cesium carbonate → 5-(Chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(chloromethyl)-1,3-oxazolidin-2-one (136 mg), 2-bromo-5-chloropyridine (192 mg), cesium carbonate (489 mg), bispalladium tribenzylideneacetone (137 mg) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (260 mg) in 1 ml of dioxane was stirred at 85° C. for 12 h. The sample was then cooled to room temperature, and filtered through a plug of silica gel (5×10 ml) eluting with ethyl acetate (50 ml). The eluent was concentrated in vacuo to provide a clear reddish-brown liquid, which was purified via column chromatography on a Biotage Horizon 40M column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 4 column volumes to provide the title compound (204 mg, 83%). Mass spectrum (ESI) 249.0 (M+2). 1H NMR (500 MHz, CDCl3): δ 8.28 (d, J=2.5 Hz, 1H), 8.20 (d, J=8.9 Hz, 1H), 7.68 (dd, J=9.0, 2.6 Hz, 1H), 4.90 (m, 1H), 4.35 (dd, J=8.9, 11.0 Hz, 1H), 4.17 (dd, J=5.7, 10.8 Hz, 1H), 3.78 (m, 2H).

Provenance & Evidence