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While mechanosynthesis of the target compound, 1-[2-(1H-indol-3-yl)-ethyl]-pyrrole-2,5-dione, C14 H12 N2 O2, did not yield the desired product, it instead resulted in an open intermediate. On the other hand, synthesis starting from the activated maleic anhydride yielded the final maleimide compound. The outcome of the mechanosynthesis has been evaluated by powder X-ray diffraction, and structures of both the final product and open intermediate have been confirmed using single-crystal crystallography.