Scheme 17.

^a(i) Br₂, CH₂Cl₂, −5 to −2 °C, 98% (ii) ethyl diazoacetate, BF₃·OEt₂, CH₂Cl₂, −5 to 0 °C, 72% (iii) 3N aq. HCl, dioxane, 100 °C, 90% (iv) NaN₃, DMF, 80% (v) LiAlH₄, THF, 0 °C, 52% (vi) picolinic acid, EDC, HOBt, NEt₃, CH₂Cl₂, 80% (vii) Dess-Martin periodinane, CH₂Cl₂, 92% (viii) Burgess' reagent, THF, 150 °C, μw, 45 minutes, 78% (ix) 48% aq. HBr, 100 °C, 74% (x) 3-bromo-5-fluorobenzonitrile, Pd₂ (dba)₃, XANTPHOS, KO^tBu, PhMe, μw, 100 °C, 22%