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Reagents and conditions: (a) DMF-DMA, reflux; (b) 56, NaOH, iPrOH, reflux; (c) Pd(PPh3)4, 4-pyridineboronic acid, K2CO3, 1,4-dioxane, 80 °C; (d) m-toluidine, p-TsOH, 1,4-dioxane, reflux; (e) m-toluidine, Pd(OAc)2, BINAP, NaOtBu, toluene, DMF, 90 °C; (f) m-bromotoluene, Pd(OAc)2, BINAP, NaOtBu, toluene, DMF, 90 °C. $ = commercially available.
