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Development of Scalable Manufacturing Routes to AZD1981. Application of the Semmler−Wolff Aromatisation for Synthesis of the Indole-4-amide Core

Sulur, Manjunatha, Sharma, Parhalad, Ramakrishnan, Ravi, Naidu, Ravi, Merifield, Eric, Gill, Duncan M., Clarke, Adrian M., Thomson, Colin, Butters, Michael, Bachu, Sreekanth, Benison, Colin H., Dokka, Nagaraju, Fong, Emily R., Hose, David R.J., Howell, Gareth P., Mobberley, Siobhan E., Morton, Simon C., Mullen, Alexander K., Rapai, Jayan and Tejas, Bharathi (2012) Development of Scalable Manufacturing Routes to AZD1981. Application of the Semmler−Wolff Aromatisation for Synthesis of the Indole-4-amide Core. Organic Process Research and Development, 16 (11). pp. 1746-1753. ISSN 1083-6160

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Abstract

A safe and efficient synthesis of AZD1981 is described in which the indole 4-amide core is formed by a Semmler− Wolff aromatisation of a cyclohexenone oxime fused to a pyrrole ring. The substrate was obtained via Paal−Knorr pyrrole synthesis, followed by incorporation of the key 3-arylthio substituent by reaction with 4-chlorophenylsulfenyl chloride. In this manner, the 1,2,3,4-substitution pattern of the AZD1981 core was regiospecifically established in a concise and efficient telescoped sequence. Accordingly, AZD1981 was obtained in 40% overall yield in six chemical steps, with two isolated crystalline intermediates.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Duncan Gill
Date Deposited: 04 Jul 2013 14:27
Last Modified: 30 Nov 2016 20:19
URI: http://eprints.hud.ac.uk/id/eprint/17883

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