Cesium carbonate → HCID 68109336, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of step B (560 mg, 1.39 mmol), sodium benzenesulfinate (275 mg, 1.67 mmol), di-palladium-tris(dibenzylideneacetone) (179 mg, 0.19 mmol), cesium carbonate (683 mg, 2.09 mmol) and xantphos (225 mg, 0.39 mmol) were suspended in anhydrous toluene (20 mL). The reaction flask was purged with argon and heated to 110° C. for 6 h. After cooling to ambient temperature, the reaction was diluted with dichloromethane and filtered through a celite bed. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 4:1 hexanes/ethyl acetate) to give tert-butyl 6-chloro-4-methyl-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-e]pyridine-2(1H)-carboxylate (190 mg, 29%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.01-7.93 (m, 3H), 7.84 (s, 1H), 7.61-7.47 (m, 3H), 4.63-4.47 (m, 2H), 4.08-3.75 (m, 1H), 3.58-3.27 (m, 1H), 3.21-3.08 (m, 1H), 1.51 (s, 9H), 1.33 (d, J=6.9 Hz, 3H).

Provenance & Evidence