4-Chloropyridine → HCID 67036357, compound

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Reaction Steps

The present invention is directed to an improved method for preparing 4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester (I); more particularly, to its synthesis in three steps. The first step comprises a boronic acid formation by treatment of (4-fluoro-benzyl)-carbamic acid tert-butyl ester under boronation conditions. The second step involves reacting the resultant 5-((tert-butoxycarbonyl)aminomethyl)-2-fluorobenzeneboronic acid of the first step with a 4-halo-pyridine such as 4-chloro-pyridine or 4-bromo-pyridine under Suzuki coupling conditions to yield (4-fluoro-3-pyridin-4-yl-benzyl)-carbamic acid tert-butyl ester. The third step involves employing selective hydrogenation conditions on the product of the second step to yield compound I. The invention is also directed to the intermediates 5-((tert-butoxycarbonyl)aminomethyl)-2-fluorobenzeneboronic acid (compound 11), and (4 fluoro-3-pyridin-4-yl-benzyl)-carbamic acid tert-butyl ester (compound 13).

Provenance & Evidence