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Reagents and conditions: (a) Pb(OAc)4, AcOH, Cu(OAc)2 62%, (b) HOCH2COOBn, 20% TFA in CH2Cl2, 59%, (c) 15% morpholine in DMF; 10% Pd–C/H2 20 PSI, 69%, (d) DMF, DIPEA 63%, (e) 10, DMTMM, TEA, 36%, (f) 12, 4% HCl in DMF, 48%, (g) 15% morpholine in DMF; 19, DIPEA, 42%, (h) DMTMM 68%, (i) 10% Pd–C/H2 20 PSI, 94%, (j) DIPEA 55%, (k) 20% TFA in CH2Cl2, 56%, (l) 15% morpholine in DMF; 28, TEA, DMTMM, 24%.
