123412-95-3

Upstream product

• 402-65-3 2-fluoropyridine-4-carboxylic acid 
• 64-17-5 ethanol 
• 1570-45-2 isonicotinic acid ethylester 
• 695-34-1 2-Amino-4-methylpyridine 
• 461-87-0 2-fluoro-4-methylpyridine 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 131747-60-9 (2-fluoropyridin-4-yl)methanol 
• 369-24-4 2-fluoro-isonicotinic acid hydrazide 

Relevant academic research and scientific papers

Electrolytic partial fluorination of organic compounds: Part 26. Anodic monofluorination of ethyl isonicotinate

Anodic fluorinations of ethyl isonicotinate (1) and related compounds have been attempted. Desired fluorinated product, 2-fluoroisonicotinate (2) was obtained in reasonable yield by direct anodic monofluorination of ethyl isonicotinate 1. The yield of 2 and the conversion of the electrochemical reaction could be improved by applying relatively lower anodic potential and by increasing the concentration of supporting electrolyte Et3N · 3HF.

Synthesis of Functionalized Pyridines via a Regioselective Oxazoline Promoted C-H Amidation Reaction

The first Rh-catalyzed C-H amidation of pyridines is reported. The incorporation of a substituent at the C2 position both is crucial to the success of this transformation and provides considerable scope for further elaboration of the resulting products. Among these compounds, 2-chloropyridines allow access to a selection of intermediates including a versatile azaquinazoline scaffold.

C-H FLUORINATION OF HETEROCYCLES WITH SILVER (II) FLUORIDE

The present invention provides compositions and methods for the selective C-H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C-H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C-H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.

Selective C-H fluorination of pyridines and diazines inspired by a classic amination reaction

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochemicals, and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. We present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using commercially available silver(II) fluoride. The reactions occur at ambient temperature within 1 hour with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

Single photon emission computed tomography/positron emission tomography imaging and targeted radionuclide therapy of melanoma: New multimodal fluorinated and iodinated radiotracers

This study reports a series of 14 new iodinated and fluorinated compounds offering both early imaging (123I, 124I, 18F) and systemic treatment (131I) of melanoma potentialities. The biodistribution of each 125I-labeled tracer was evaluated in a model of melanoma B16F0-bearing mice, using in vivo serial γ scintigraphic imaging. Among this series, [125I]56 emerged as the most promising compound in terms of specific tumoral uptake and in vivo kinetic profile. To validate our multimodality concept, the radiosynthesis of [18F]56 was then optimized and this radiotracer has been successfully investigated for in vivo PET imaging of melanoma in B16F0- and B16F10-bearing mouse model. The therapeutic efficacy of [131I]56 was then evaluated in mice bearing subcutaneous B16F0 melanoma, and a significant slow down in tumoral growth was demonstrated. These data support further development of 56 for PET imaging (18F, 124I) and targeted radionuclide therapy ( 131I) of melanoma using a single chemical structure.

Labelled analogues of halobenzamides as multimodal radiopharmaceuticals and their precursors

The present invention relates to the compound of formula (I): in which R1 represents a hydrogen atom, an optionally labelled halogen atom, a radionuclide or a Sn[(C1-C4)alkyl]3 group, Ar represents an aryl group

Synthesis, Chemistry, and Antineoplastic Activity of α-Halopyridinium Salts: Potential Pyridone Prodrugs of Acylated Vinylogous Carbinolamine Tumor Inhibitors

A series of 4- and 5-methyl>-1H-pyrrolizin-5-yl>-2-halopyridinium iodides were synthesized.The rates of hydrolysis of the α-halopyridinium salts to the corresponding pyridones, and the reactivities of the carbamate moieties were studied as a function of pH, buffer composition, and ionic strength.The 4- and 5-pyrrolizinyl-2-halopyridinium iodides and the corresponding pyridones were evaluated against P388 lymphocytic leukemia in vivo.The α-fluoropyridinium compounds were active but the α-chloro compounds were not.This activity was correlated with the rates of hydrolysis of the α-halopyridinium compounds to the active pyridone.Compounds that were active in the P388 screen were evaluated in L1210 leukemia, M5076 carcinoma, and MX-1 mammary xenograft assays in mice.