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

A facile three-step synthesis of 2-(2-aminophenyl)pyrrole (1) and 2-(2- aminomethylphenyl)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 Pdcatalyzed cross coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron-donating and electron-withdrawing substituents, 5a-g. Moreover, Pdcatalyzed coupling of o-bromoaniline and 3 could be applied for the one step preparation of pyrrolo[1, 2-c]quinazolin-5(6H)-one (8). Keywords: Synthesis of aminoarylpyrroles, Suzuki-Miyaura coupling, 2-(o-substituted aryl)pyrroles, Pd-catalyzed cross coupling

synthesis of aminoarylpyrroles; Suzuki-Miyaura coupling; 2-(o-substituted aryl)pyrroles; Pd-catalyzed cross coupling

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