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

Author:

Sulur Manjunatha1,Sharma Parhalad1,Ramakrishnan Ravi1,Naidu Ravi1,Merifield Eric2,Gill Duncan M.2,Clarke Adrian M.2,Thomson Colin2,Butters Michael3,Bachu Sreekanth1,Benison Colin H.3,Dokka Nagaraju1,Fong Emily R.2,Hose David R. J.3,Howell Gareth P.2,Mobberley Siobhan E.2,Morton Simon C.2,Mullen Alexander K.3,Rapai Jayan1,Tejas Bharathi1

Affiliation:

1. Pharmaceutical Development, AstraZeneca India Pvt. Ltd., Hebbal, Off Bellary Road, Bangalore 560024, India

2. Pharmaceutical Development, AstraZeneca R & D Charnwood, Bakewell Road, Loughborough, Leicestershire, LE11 5RH, United Kingdom

3. Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield, SK10 2NA, United Kingdom

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Reference29 articles.

1. Bonnert, R.; Rasul, R.Novel substituted 3-sulfur indoles. WO 2004106302 A1, 2004.

2. A novel method of indole ring system construction: One-pot synthesis of 4- and 6- nitroindole derivatives via base promoted reaction between 3-nitroaniline and ketones

3. Synthesis of heterocyclic compounds via vicarious nucleophilic substitution of hydrogen

4. Conley, R. T.; Ghosh, S.InMechanisms of Molecular Migrations;Thyagarajan, B. S., Ed.Interscience:New York, 1971; Vol.4, p251.

5. Ainge, D.; Butters, M.; Merifield, E.; Ramakrishnan, R.; Rayapati, R.; Sharma, P.; Thomson, C.Intermeditaes and processes for the preparation of 4-(acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-1H-indole-1-acetic acid. WO2011004182A1, 2011.

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