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(a) SOCl2 (3.0 eq), toluene, DMF, reflux, 2–3 hours: then 3-iodoaniline (1.2 eq), Et3N (2.0 eq), THF, 10 minutes at 0 °C, 20 hours at 22 °C; 98% yield. (b) NaIO4 in H2O (1.6 eq), MeOH, 50 °C, 4–5 hours; 96% yield. (c) Phenyl boronic acid (1.2 eq), K2CO3 (3.3 eq), [Pd(PPh3)4] (0.025 eq), H2O:THF (1:2), 80 °C, 18–22 hours; 80–87% yield. (d) SOCl2 (1.3 eq), DCM, 50 °C, 1.5 hours; 35–74% yield.
