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Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives

✍ Scribed by Marija Alešković; Nikola Basarić; Kata Mlinarić-Majerski

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
233 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A facile three‐step synthesis of 2‐(2‐aminophenyl)pyrrole (1) and 2‐[(2‐aminomethyl)phenyl]pyrrole (2) is reported by use of Suzuki coupling of N‐Boc‐pyrrol‐2‐yl boronic acid (3) and o‐substituted aryl halogenides, followed by hydrogenation. The Pd‐catalyzed cross‐coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron‐donating and electron‐withdrawing substituents, 5a, 5b, 5c, 5d, 5e, 5f, 5g. Moreover, Pd‐catalyzed coupling of o‐bromoaniline and 3 could be applied for the one‐step preparation of pyrrolo[1,2‐c]quinazolin‐5(6__H__)‐one (8). J. Heterocyclic Chem., (2011).

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