Cesium carbonate → HCID 59409862, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(chloromethyl)-5-methyl-1,3-oxazolidin-2-one (1.50 g, INTERMEDIATE 16), 2-bromo-5-chloropyridine (1.92 g), cesium carbonate (4.89 g), bispalladium tribenzylideneacetone (1.37 g) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.30 g) in 25 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 (15×15 ml) of silica gel eluting with ethyl acetate. The eluent then was concentrated in vacuo and purified via column chromatography on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 60% ethyl acetate in hexanes (over 10 column volumes), and held at 60% ethyl acetate for 4 column volumes to provide the title compound (1.01 g, 39%). Mass spectrum (ESI) 262.9 (M+2).). 1H NMR (500 MHz, CDCl3): δ 8.27 (d, J=2.5 Hz, 1), 8.21 (d, J=8.9 Hz, 1H), 7.68 (dd, J=8.9, 2.5 Hz, 1H), 4.31 (d, J=10.8 Hz, 1H), 3.95 (d, J=10.7 Hz, 1H), 3.73 (d, J=11.7 Hz, 1H), 3.63 (d, J=11.7 Hz, 1H), 1.66 (s, 3H).

Provenance & Evidence