Water → 5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-7-methyl-5H-imidazo[2,1-a]isoindole

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5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-5H-imidazo[2,1-a]isoindol-7-yl trifluoromethanesulfonate (50 mg), methylboronic acid (8 mg), K2CO3 (37 mg), and PdCl2(dppf)-CH2Cl2 adduct (8 mg) were combined in 1,4-dioxane (400 μL):H2O (40.0 μL). The mixture was degassed (3× pump/N2) then heated to 100° C. After 3 h the mixture was cooled to room temperature and concentrated. The residue was taken up in DMF, filtered using a 0.45 μm PTFE syringe filter, then purified by preparative reversed-phase HPLC (21×100 mm Phenomenex Gemini (5-95% ACN/water containing 0.05% NH4OH over 20 min at 20 mL/min) to give a light grey solid (16 mg): 1H-NMR (400 MHz, CDCl3) δ 7.71 (d, J=7.79 Hz, 1 H), 7.27 (m, 3 H), 7.19 (m, 1 H), 7.12 (dd, J=3.66 and 5.04 Hz, 2 H), 7.03 (bs, 1 H), 6.93 (dd, J=1.19 and 7.88 Hz, 1 H), 3.89 (m, 1 H), 3.41 (m, 1 H), 3.20-2.75 (m, 2 H), 2.34 (d, J=2.74 Hz, 3 H), 1.97-1.63 (m, 2 H), 1.50 (m, 4 H), 1.17 (dd, J=6.32 and 8.43 Hz, 3 H), 0.86 (dd, J=6.50 and 27.1 Hz, 3 H); HRMS (M+H)+ calculated 434.1994. found 434.1993.

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