Scheme 1.

Synthesis of 7-(2-Aminopyridyl)tetrahydroquinoline Analogs^a

^aReagents and conditions. (a) NaOMe, MeOH; (b) Ph₂CNH, Pd(OAc)₂, BINAP, Cs₂CO₃, toluene, 100 °C; (c) (i) Pd(PPh₃)₄, Cs₂CO₃, toluene/H₂O, 100 °C; (ii) HCl, THF; (d) H₂, Pd, MeOH; (e) Br₂, AcOH (40b) or NBS, CH₃CN (40c–d °C.); (f) Pd(PPh₃)₄, aq. Na₂CO₃ or Cs₂CO₃, dioxane, 80–100 °C.