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. 2011 Apr 15;2(8):411–432. doi: 10.1021/cn2000266

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Scheme 17 — (i) Br₂, CH₂Cl₂, −5 to −2 °C, 98%; (ii) ethyl diazoacetate, BF₃·OEt₂, CH₂Cl₂, −5 to 0 °C, 72%; (iii) 3 N 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 min, 78%; (ix) 48% aq. HBr, 100 °C, 74%; (x) 3-bromo-5-fluorobenzonitrile, Pd₂(dba)₃, XANTPHOS, KO^tBu, PhMe, μw, 100 °C, 22%.