Early Amidation Approach to 3-[(4-Amido)pyrrol-2-yl]-2-indolinones

• Published in: Journal of organic chemistry Vol. 68; no. 16; pp. 6447 - 6450
• Main Authors: Manley, Jerad M, Kalman, Monica J, Conway, Brian G, Ball, Cynthia C, Havens, Jeffrey L, Vaidyanathan, Rajappa
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.08.2003; Amer Chemical Soc
• Subjects: Amides - chemical synthesis; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Indicators and Reagents; Indoles - chemical synthesis; Organic chemistry; Physical Sciences; Preparations and properties; Pyrroles - chemical synthesis; Pyrroles - chemistry; Science & Technology; Zinc; ESTER; ANALOGS; DERIVATIVES; Diamine; Four membered ring; Nitrogen heterocycle; Lactam; Carboxamide; Lactone; Indole derivatives; Chemical synthesis; Hydrogenation; Amidation; Ethylenic compound; Pyrrole derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo034304q

A new synthesis of 3-[(4-amido)pyrrol-2-yl]-2-indolinones has been developed, where the amide side chain was installed prior to pyrrole formation. This strategy precludes the need to use any coupling reagents to install the amide side chain. This process includes a zinc-free alternative to the Knorr pyrrole synthesis.