Cesium carbonate → 9-(8-Aza-bicyclo[3.2.1]oct-3-ylidene)-5-phenyl-9H-xanthene-3-carboxylic acid diethylamide

Participants

Reaction Steps

A mixture of 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-bromo-9H-xanthene-3-carboxylic acid diethylamide (0.170, 0.363 mmol), phenylboronic acid (0.049 g, 0.40 mmol) and cesium carbonate (0.236 g, 0.726 mmol) in dioxane (4 mL) and ethanol (1 mL) was treated with dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (13 mg), and the resulting mixture was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, and the inorganics removed by filtration and washed successively with dioxane, ethanol and dichloromethane. The solvents were evaporated in vacuo. The residue was purified by reverse phase (C18) preparative HPLC, using a gradient of acetonitrile (10% to 90%) in water with trifluoroacetate (0.1%) as the eluant to give the title compound (0.153 g) as a colorless solid. MS: m/z 465.3 (MH+). 1H NMR (DMSO-d6): δ 1.05-1.20 (br m, 6H0, 1.31 d, 2H, J=8.2 Hz), 1.75-1.85 (br m, 2H), 2.90-3.10 (m, 4H), 3.15-3.50 (br m, 4H), 4.03 br s, 2H), 7.10 (d, 1H, J=1.5 Hz), 7.20 (d of d, 1H, J=1.5 & 7.9 Hz), 7.32 (t, 1H, J=7.5 Hz), 7.40-7.63 (m, 8H), 8.83 (br s, 1H0 and 9.16 (br d, 1H).

Provenance & Evidence