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Cyclobutanecarboxylic acid-based approaches to the advanced intermediate 39 needed for assembly of apalutamide. Reaction conditions: (a) DMF, K2CO3, CuCl, H2O, 100–105 °C; (b) i-Pr2Net, Et3N, CH2Cl2, reflux; (c) MeI, DMF, K2CO3, rt; (d) 18, DMSO, 2-PrOAc, 90 °C.
