An Improved Kilogram-Scale Synthesis of 2‑Bromo-4-nitro‑1H‑imidazole: A Key Building Block of Nitroimidazole Drugs

An efficient two-step method for the synthesis of 2-bromo-4-nitroimidazole, 6, a key building block for nitroimidazole drugs, has been developed. The synthesis involves dibromination of 4-nitroimidazole 10 followed by selective debromination using in situ reductive deiodination strategy. The reactio...

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Published in:Organic process research & development 2013-09, Vol.17 (9), p.1149-1155
Main Authors: Pedada, Srinivasa Rao, Satam, Vijay S, Tambade, Pawan J, Kandadai, Srinivas A, Hindupur, Rama Mohan, Pati, Hari N, Launay, Delphine, Martin, Denis
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container_issue 9
container_start_page 1149
container_title Organic process research & development
container_volume 17
creator Pedada, Srinivasa Rao
Satam, Vijay S
Tambade, Pawan J
Kandadai, Srinivas A
Hindupur, Rama Mohan
Pati, Hari N
Launay, Delphine
Martin, Denis
description An efficient two-step method for the synthesis of 2-bromo-4-nitroimidazole, 6, a key building block for nitroimidazole drugs, has been developed. The synthesis involves dibromination of 4-nitroimidazole 10 followed by selective debromination using in situ reductive deiodination strategy. The reactions are facile, safe, and easy to scale up. The large-scale applicability of this improved method was tested by conducting the reactions on kilogram scale to produce the desired product in high yield and quality.
doi_str_mv 10.1021/op400095f
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title An Improved Kilogram-Scale Synthesis of 2‑Bromo-4-nitro‑1H‑imidazole: A Key Building Block of Nitroimidazole Drugs
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