36255-28-4

Usage

Uses

Used in Pharmaceutical Research:
3-Nitro-6-bromoquinoline is used as a building block for the synthesis of biologically active compounds, contributing to the development of new drugs due to its potential biological activities.
Used in Medicinal Chemistry:
3-Nitro-6-bromoquinoline is used as a subject of interest for its antimicrobial and antitumor properties, making it a valuable compound in the discovery and design of novel therapeutic agents.
It is important to handle 3-Nitro-6-bromoquinoline with care, as it is a potential hazardous material, and its use should be conducted under appropriate safety measures.

Upstream product

• 5332-25-2 6-bromoquinoline 

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.