Development of Synthetic Route for 3-Amino-5-halo-2-iodobenzoates: Versatile Starting Materials in Pharmaceuticals Synthesis

초록

A novel synthetic route to 3-amino-5-halo-2-iodobenzoates, which are used as versatile starting materials in the synthesis of pharmaceuticals, was developed using commercially available 2-aminobenzoates bearing a suitable halogen atom at the C5 position as the starting material. Synthesis was initiated with the introduction of a nitro group at the C3 position of the appropriate 2-aminobenzoates, forming 2-amino-3-nitrobenzoates with a C5-halogen atom. The subsequent conversion of the C2-amino group to an iodide yielded 5-halo-2-iodo-3-nitrobenzoates, which were further converted into the desired 3-amino-5-halo-2-iodobenzoates by reducing the C3-nitro group to an amino group. It is worth noting that this transformation can be conducted on a 50 mmol scale, and the desired benzoate compounds were obtained in good yield, demonstrating the practical applicability of this protocol. A novel synthetic route for 3-amino-5-halo-2-iodobenzoates was developed from commercially available 2-amino-5-halobenzoates Nitration at the C3 position afforded 2-amino-5-halo-3-nitrobenzoates. Subsequent conversion of the C2-amino group to an iodide, followed by reduction of the C3-nitro group to an amino group, yielded the desired benzoates. This protocol is demonstrated on a 50 mmol scale, showcasing its practical utility.+ image

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