916314-03-9

Basic information

• Product Name: 5-fluoropyridine-2-carboxamide
• Synonyms: 5-fluoropyridine-2-carboxamide;5-(Fluoro-18F)-2-pyridinecarboxamide
• CAS NO: 916314-03-9
• Molecular Formula: C6H5FN2O
• Molecular Weight: 140.12
• Mol File: 916314-03-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-fluoropyridine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-fluoropyridine-2-carboxamide(916314-03-9)
• EPA Substance Registry System: 5-fluoropyridine-2-carboxamide(916314-03-9)

Safety Data

• Hazardous Substances Data: 916314-03-9(Hazardous Substances Data)

Usage

General Description

5-Fluoropyridine-2-carboxamide is a chemical compound with the molecular formula C6H4FN3O. It is known for its pharmaceutical applications, particularly in the field of oncology, as it is used in the synthesis of anti-cancer drugs such as Tegafur and Caracemide. 5-Fluoropyridine-2-carboxamide acts as a precursor in the production of these anti-cancer agents, which work by inhibiting the growth and spread of cancer cells in the body. Its structure and properties make it a valuable building block in the development of new and improved cancer treatments. Moreover, it is also used in various other chemical reactions and synthesis processes in the pharmaceutical and chemical industries.

Upstream product

• 90145-48-5 5-bromo-2-pyridinecarboxamide 

Relevant articles and documents

Synthesis of fluorine-18-labelled 5- and 6-fluoro-2-pyridinamine

A one-pot radiosynthesis method to prepare the new fluorine-18-labelled fluoropyridine derivatives 5-[18F]fluoro-2-pyridinamine and 6-[ 18F]fluoro-2-pyridinamine in two to three reaction steps was developed. The first step consisted of no-carrier-added nucleophilic aromatic substitution of commercially available halogen-substituted 2-pyridinecarboxamide or 2-pyridinecarbonitrile derivatives with K[18F]F-K222 in DMSO at 150-180°C. The [18F]fluoride incorporation yields ranged from 67 to 98% for all studied precursor molecules. It is remarkable that 5-bromo-2-pyridinecarbonitrile gave almost quantitative [18F] fluoride incorporation at the meta-position (5-position) of the pyridine ring after only 5 min of heating at 150°C. After base-catalysed hydrolysis of the [18F]fluorinated pyridinecarbonitriles into their corresponding carboxamides, the latter were transformed in a Hofmann-type rearrangement reaction into the respective amines by treatment of crude reaction mixtures with bromine and aqueous base (20-30% conversion yield). Reaction mixtures were purified by reversed-phase semipreparative HPLC followed by strong cation exchange solid-phase extraction to afford 5-[18F]fluoro-2- pyridinamine and 6-[18F]fluoro-2-pyridinamine in non-decay-corrected radiochemical yields of 6-10% in a total synthesis time of 83-112 min. The preparation of 5-[18F]fluoro-2-pyridinamine is one of very few examples demonstrating the feasibility of nucleophilic meta-[ 18F]fluorination of a pyridine derivative. Both 5-[ 18F]fluoro-2-pyridinamine and 6-[18F]fluoro-2-pyridinamine are new potentially useful radiolabelled synthons for radiopharmaceutical chemistry. Copyright