Cesium carbonate → HCID 90410529, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product of Example 1, step (g) (0.056 g, 0.21 mmol) in dioxane (1.5 ml) under argon was added iodobenzene (0.026 ml, 0.23 mmol), Cs2CO3 (0.15 g, 0.45 mmol), CuI (0.002 g, 0.01 mmol), and (+)-trans-1,2-diaminocyclohexane (0.005 ml, 0.04 mmol). The reaction mixture was heated to 100° C. until LCMS indicated the reaction was complete (usually 16 hours). The reaction mixture was cooled to RT, diluted with DCM, and filtered through celite. The solvent was evaporated in vacuo and the residue purified by flash silica-gel chromatography (gradient elution: 0 to 50% EtOAc in hexanes) to give the sub-titled compound as a colorless oil (0.066 g). 1H NMR (CD3OD) δ 7.53-7.39 (m, 3H), 7.38-7.32 (m, 2H), 6.92 (d, J=3.0 Hz, 1H), 6.38 (d, J=3.0 Hz, 1H), 4.18-4.06 (m, 2H), 3.68-3.58 (m, 2H), 3.48-3.42 (m, 2H), 3.00-2.94 (m, 2H), 2.54-2.46 (m, 2H), 1.30-1.16 (m, 3H); MS: ESI (positive): 341 (M+H).

Provenance & Evidence