Abstract:
Treatment of indomethacin with N-bromosuccinimide in AcOH results in bromination in aromatic positions 4 and 6, while the use of tetrachloromethane allows ultimate bromination at the C(2) Me group of the indole moiety to proceed.
Citation:
A. V. Ivachtchenko, P. M. Yamanushkin, O. D. Mitkin, O. I. Kiselev, “Bromination of indomethacin”, Mendeleev Commun., 20:2 (2010), 111–112
Linking options:
https://www.mathnet.ru/eng/mendc3007
https://www.mathnet.ru/eng/mendc/v20/i2/p111
This publication is cited in the following 12 articles:
Hong Sun, Zhongyuan Wang, Liyuan Deng, Weiyin Hu, Tianhui Liao, Xin Zhao, Zhixu Zhou, Huifang Chai, Chunshen Zhao, “Synthesis, crystal structure, and DFT study of a new pyrido[2,3-d]pyrimidine compound 1-(4-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy) phenyl)-3-(2,4-difluorophenyl)urea”, Molecular Crystals and Liquid Crystals, 742:1 (2022), 10
R. -S. Luo, S. -N. Mao, C. -J. Liu, Z. -X. Zhou, Z. -Y. Huang, “SYNTHESIS, X-RAY STRUCTURE ANALYSIS, AND VIBRATIONAL SPECTRAL STUDIES OF 1-(3-((6-BROMOPYRIDO[2,3-d]PYRIMIDIN-4-YL) OXY)PHENYL)-3-CYCLOPENTYLUREA”, J Struct Chem, 63:1 (2022), 37
Qingmei Wu, Zhaopeng Zheng, Wenjun Ye, Qian Guo, Tianhui Liao, Di Yang, Chunshen Zhao, Weike Liao, Huifang Chai, Zhixu Zhou, “Synthesis, crystal and molecular structure, vibrational spectroscopic, DFT and molecular docking of 4-(2-chlorobenzyl)-1-(4‑hydroxy-3- ((4-hydroxypiperidin-1-yl) methyl-5-methoxyphenyl)-[1,2,4] triazolo [4,3-a] quinazolin-5(4H)-one”, Journal of Molecular Structure, 1247 (2022), 131367
Hong Sun, Liyuan Deng, Weiyin Hu, Tianhui Liao, Weike Liao, Huifang Chai, Chunshen Zhao, “Synthesis, crystal structure, vibrational properties and DFT studies of 4-(furan-2-ylmethyl)-1-(thiomorpholinomethyl)-[1,2,4]triazolo[4,3-a]quinazon-5(4H)-one”, Journal of Molecular Structure, 1248 (2022), 131395
Y. Liu, Z. Zheng, H. Deng, Q. Ren, Z. Zhou, C. Zhao, H. Chai, “SYNTHESIS AND CHARACTERIZATION OF A NEW COMPOUND 4-(2-CHLOROBENZYL)IMIDAZO[1,2-a] QUINAZOLIN-5(4H)-ONE: DFT STUDY, CRYSTAL STRUCTURE, MEP, AND HOMO–LUMO VALUES”, J Struct Chem, 62:8 (2021), 1285
Zhi-xu Zhou, Qing-mei Wu, Zhu-yan Huang, De-hou Yu, Hong-guang Lu, “Synthesis, crystal structure, DFT, molecular docking and antitumor activity of 4-(2-chlorobenzyl)-1-(5-fluoro-2-hydroxy-3-((4-methylpiperidin-1-yl)methyl)phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one”, Res Chem Intermed, 47:9 (2021), 3609
Ye Liu, Yongli Zhao, Qian Ren, Zhixu Zhou, Huifang Chai, Chunshen Zhao, “Synthesis, crystal structure and DFT study of a novel planar bipyridyl compound 6,6′-bis(trifluoromethyl)-3,3′-bipyridine”, Journal of Molecular Structure, 1208 (2020), 127869
Dali Luo, Lanlan Ma, Zhixu Zhou, Zhuyan Huang, “Synthesis, single crystal X-ray analysis, and vibrational spectral studies of ethyl 6-bromo-5-((5-bromopyrimidin-2-yl)oxy)-2-((2, 6-dimethylmorpholino)methyl)-1-methyl-1H-indole-3-carboxylate”, Journal of Molecular Structure, 1198 (2019), 126857
Konstantin V. Balakin, Rosanna Filosa, Sergey N. Lavrenov, Arthur S. Mkrtchyan, Maxim B. Nawrozkij, Ivan A. Novakov, “Arbidol: a quarter-century later. Past, present and future of the original Russian antiviral”, Russian Chem. Reviews, 87:6 (2018), 509–552
A. V. Ivashchenko, P. M. Yamanushkin, O. D. Mit'kin, V. M. Kisil', O. M. Korzinov, V. Yu. Vedenskii, I. A. Leneva, E. A. Bulanova, V. V. Bychko, I. M. Okun', “Synthesis and Antiviral Activity of Ethyl 1,2-dimethyl-5-Hydroxy-1H-Indole-3-carboxylates and Their Derivatives”, Pharm Chem J, 47:12 (2014), 636
A. V. Ivashchenko, P. M. Yamanushkin, O. D. Mit'kin, I. A. Leneva, I. T. Fedyakina, “Synthesis and antiviral activity of functionally substituted indole-3-acetic acids”, Pharm Chem J, 45:5 (2011)
Alexandre V. Ivachtchenko, Pavel M. Yamanushkin, Oleg D. Mitkin, Oleg I. Kiselev, “ChemInform Abstract: Bromination of Indomethacin.”, ChemInform, 41:50 (2010)
Contact us: