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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Bibliographic Details
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
Format: Article
Language:English
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op400095f