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Synlett 2011(15): 2185-2186  
DOI: 10.1055/s-0030-1261175
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple and Efficient Protocol to 1,2,4-Substituted Pyrroles via a Sonogashira Coupling-Acid-Catalyzed Cyclization

Da Zhu, Jie Zhao, Yuxiu Wei, Hongwei Zhou*
Department of Chemistry, Zhejiang University, (Campus Xixi), Hangzhou 310007, P. R. of China
Fax: +86(571)88920271; e-Mail: zhouhw@zju.edu.cn;
Further Information

Publication History

Received 3 May 2011
Publication Date:
10 August 2011 (online)

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Abstract

A facile and efficient protocol for the synthesis of 1,2,4-substituted pyrrole derivatives was developed. As a result of the ready availability of materials and the simple operation, this type of reaction should have potential utility in organic synthesis.

Key words

pyrroles - Sonogashira reaction - gallium triflate - cyclization - 2-bromoallylamine

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General Procedure for the Synthesis of 3a
To a solution of 1a (0.5 mmol) and 2a (0.6 mmol) in 5 mL of THF was charged CuI (2 mg. 0.01 mmol) and PdCl2(PPh3)2 (7 mg, 0.01 mmol), then charged 1 mL of Et3N under an N2 atmosphere at r.t. The reaction was monitored by TLC until it went to completion (4 h). The reaction mixture was quenched with H2O, extracted with Et2O (30 mL), and dried over anhyd Na2SO4. After evaporation of the Et2O, chromatography on silica gel (PE) of the crude product afforded 3a. ¹H NMR (400 MHz, CDCl3): δ = 7.35-7.32 (m, 4 H), 7.27-7.23 (m, 1 H), 6.52-6.52 (d, J = 0.8 Hz, 1 H), 6.01-6.00 (d, J = 2.0 Hz, 1 H), 3.84-3.81 (t, J = 7.4 Hz, 2 H), 2.12 (s, 3 H), 1.64-1.56 (m, 2 H), 1.23-1.17 (q, J = 7.5 Hz, 2 H), 0.83-0.79 (t, J = 7.4 Hz, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 134.6, 134.2, 129.1, 128.6, 126.9, 120.4, 118.7, 110.3, 47.0, 34.0, 20.2, 14.0, 12.2. IR (neat): 1491, 1342 cm-¹. HRMS: m/z calcd for C15H19N: 213.1517; found: 213.1518.