630125-49-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-nitrobenzotrifluoride is used as an intermediate in the synthesis of Nilotinib (N465300), a medication used for the treatment of chronic myeloid leukemia (CML). It plays a crucial role in the production of this life-saving drug.
Used in Chemical Synthesis:
3-Bromo-5-nitrobenzotrifluoride is used as an efficient D-glucosamine-based copper catalyst for C-X couplings, a type of chemical reaction that forms carbon-heteroatom bonds. This application is particularly useful in the synthesis of nilotinib intermediate, contributing to the development of new and improved pharmaceutical compounds.

Upstream product

• 98-46-4 3-trifluoromethylnitrobenzene 
• 479411-92-2 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 916975-92-3 4-methyl-1-(3-nitro-5-(trifluoromethyl)-phenyl)-1H-imidazole 
• 54962-75-3 [3-bromo-5-(trifluoromethyl)phenyl]amine 
• 1365803-08-2 1-methyl-4-[3-nitro-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine 
• 1365803-07-1 4-(3-nitro-5-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine 
• 861881-13-2 3-(1-methylpiperidin-4-yl)-5-(trifluoromethyl)aniline 
• 1365803-06-0 tert-butyl 4-[3-nitro-5-(trifluoromethyl)phenyl]- 1,2,3,6-tetrahydropyridine-1-carboxylate 
• 96100-12-8 3-methyl-5-(trifluoromethyl)aniline 
• 96783-80-1 1-Methyl-3-nitro-5-trifluoromethyl-benzene 
• 1227582-49-1 3-nitro-5-(trifluoromethyl)benzene-1-sulfonyl chloride 

Relevant academic research and scientific papers

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

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.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

Method for preparing nilotinib intermediate

Disclosed in the present invention is a method for preparing nilotinib intermediate 3-(4-methyl-1H-imidazol-1-yl)-5trifluoromethyl phenylamine (I). The method comprises the following steps: taking trifluorotoluene as an initial material, and preparing the nilotinib intermediate (I) by nitration, bromization, condensation and reduction successively Compared with the prior art, the preparation method has the following advantages: a relatively high yield, the raw materials are easily obtained, a concise process and few side reactions, and is adapted to industrial production, so the development of an economic technology of the bulk drug is pro moted.

An efficient d-glucosamine-based copper catalyst for C-X couplings and its application in the synthesis of nilotinib intermediate

d-Glucosamine has been studied for C-N and C-S bond formations via cross-coupling reactions of nitrogen and sulfur nucleophiles with both aryl iodides and bromides. Imidazoles, benzimidazole, indole, pyrrolidine and diphenyl disulfide undergo reactions with aryl halides in the presence of 10 mol% d-glucosamine, 10 mol% CuI, and 2 equiv. of Cs2CO3 in DMSO-H2O at moderate temperature to give the corresponding products in good to excellent yields. Substrates bearing halides, free amino groups, trifluoromethyl and heterocycles were well tolerated. The high water solubility of the ligand enables easy catalyst removal. In addition, the application of this catalytic system for the synthesis of nilotinib intermediate was also successfully demonstrated using commercially available substrates. This journal is

PROCESS FOR THE SYNTHESIS OF ORGANIC COMPOUNDS

The present invention provides an efficient, safe and cost effective way to prepare 5 (4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine which is a key intermediate for the preparation of substituted pyrimidinylaminobenzamides of formula (II).