A new and efficient synthesis of an advanced intermediate in the preparation of a novel Insulin-like Growth Factor I Receptor (IGF-IR) signaling inhibitor is described. The new route eliminates the problematic steps found in the Discovery synthesis (length, high vacuum distillations, chromatography) and establishes the crucial 1,3-cis stereochemistry of the cyclobutane ring in the early steps. The synthesis involves 5 linear steps and provides the API starting material in an overall yield of 20% as opposed to the original approach which utilized 21 steps (including purifications) and provided the same compound in an overall yield of 8%. The challenges involved in the design and execution of this new strategy will be described.
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