- meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
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Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
- Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
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supporting information
p. 8018 - 8023
(2019/05/29)
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- Potent non-benzoquinone ansamycin heat shock protein 90 inhibitors from genetic engineering of Streptomyces hygroscopicus
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Inhibition of the protein chaperone Hsp90 is a promising new approach to cancer therapy. We describe the preparation of potent non-benzoquinone ansamycins. One of these analogues, generated by feeding 3-amino-5-chlorobenzoic acid to a genetically engineer
- Menzella, Hugo G.,Tran, Thomas-Toan,Carney, John R.,Lau-Wee, Janice,Galazzo, Jorge,Reeves, Christopher D.,Carreras, Christopher,Mukadam, Sophie,Eng, Sara,Zhong, Ziyang,Timmermans, Pieter B. M. W. M.,Murli, Sumati,Ashley, Gary W.
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supporting information; experimental part
p. 1518 - 1521
(2010/02/28)
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- Macrolactams by engineered biosynthesis
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Macrolactams are made by feeding aromatic amino acids as replacement starter units to a mutant strain of the geldanamycin-producing microorganism Streptomyces hygroscopicus var. geldanus NRRL 3602, wherein the gene cluster encoding enzymes for the biosynt
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Page/Page column 14
(2008/12/07)
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- Aminoacetamide acyl guanidines as beta-secretase inhibitors
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There is provided a series of substituted acyl guanidines of Formula (Ik) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R2, R3, R4, R5, R25, R26 and R27 as defined herein, their pharmaceutical compositions and methods of use. These compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.
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Page/Page column 17-18
(2008/06/13)
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