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Reagents and conditions: (a) CsF, DMF, 40 °C to rt, 3 d, 71%; (b) KOH, EtOH, 46%, rt, overnight; (c) chiral SFC (OJ-H, 4.6 × 100 mm, 5% MeOH/0.1% TFA/CO2, 2.5 mL/min, 100 bar); (d) HATU, iPr2NEt, 1-chloro-3,4-benzenediamine, DMF, overnight; (e) AcOH, 75 °C, 2 h, 58% over 2 steps; (f) NaOH, THF, 70 °C, 25 min, 77%; (g) Pd(OAc)2, dppf, K3PO4, EtOH, 120 °C, microwave, 5 min, 76%.
