Cesium carbonate → HCID 67085665, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of the product of step A (270 mg, 0.64 mmol), sodium benzenesulfinate (211 mg, 1.29 mmol), di-palladium-tris(dibenzylideneacetone) (59 mg, 0.06 mmol), cesium carbonate (314 mg, 0.96 mmol) and xantphos (74 mg, 0.12 mmol) under an argon atmosphere was added anhydrous toluene (4 mL). The mixture was heated at 115° C. overnight, cooled to ambient temperature, diluted with dichloromethane and filtered through celite bed. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5-isopropyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (100 mg, 38%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (s, 1H), 7.94-7.97 (m, 2H), 7.62 (d, J=8.7 Hz, 1H), 7.43-7.52 (m, 4H), 5.24 (br s, 1H), 4.69 (br s, 1H), 4.46-4.61 (m, 1H), 3.46 (br s, 1H), 2.54 (d, J=15.9 Hz, 1H), 2.25-2.35 (m, 1H), 2.12-2.23 (m, 1H), 1.95 (t, J=9.9 Hz, 1H), 1.56-1.63 (m, 1H), 1.54 (d, J=6.9 Hz, 3H), 1.50 (d, J=6.9 Hz, 3H), 1.33 (s, 9H).

Provenance & Evidence