Cesium carbonate → HCID 68109805, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 8-bromo-6-(2-hydroxypropyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (110 mg, 0.27 mmol), sodium benzenesulfinate (53 mg, 0.32 mmol), di-palladium-tris(dibenzylideneacetone) (24 mg, 0.03 mmol), cesium carbonate (131 mg, 0.40 mmol) and xantphos (31 mg, 0.06 mmol) was suspended in anhydrous toluene (8 mL). The flask was purged with argon, sealed, and heated to 120° C. for 14 h. The reaction mixture was cooled, diluted with dichloromethane, and filtered through a celite bed. The filtrate was concentrated in vacuo to give the crude product which was purified by flash column chromatography (SiO2, 4:1 hexanes/ethyl acetate) to give tert-butyl 6-(2-hydroxypropyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (50 mg, 44%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.00-7.92 (m, 3H), 7.71 (s, 1H), 7.58-7.45 (m, 3H), 4.56 (br s, 2H), 4.26-4.17 (m, 1H), 3.83 (s, 2H), 3.04 (t, J=3.9 Hz, 2H), 2.86 (br s, 2H), 1.51 (s, 9H), 1.25 (d, J=4.8 Hz, 3H).

Provenance & Evidence