2369-19-9

Usage

Chemical Properties

liquid

InChI:InChI=1/C6H6FN/c1-5-2-3-6(7)8-4-5/h2-4H,1H3

Upstream product

• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 108-99-6 3-Methylpyridine 
• 75-05-8 acetonitrile 

Downstream Products

• 403-45-2 6-fluoronicotinic acid 
• 1003-68-5 5-methyl-2-pyridone 
• 153034-78-7 2-Fluoro-3-iodo-5-methylpyridine 
• 1003-68-5 5-methyl-pyridin-2-ol 
• 1620-77-5 5-methylpicolinonitrile 
• 852510-62-4 (3-chloro-phenyl)-(2-fluoro-5-methyl-pyridin-3-yl)-methanol 
• 105827-74-5 5-(Bromomethyl)-2-fluoropyridine 
• 369-50-6 6-fluoronicotinamide 
• 434899-19-1 C₁₃H₁₂FNO 
• 65352-94-5 6-fluoronicotinoyl chloride 
• 936342-76-6 2-(4-bromo-benzyloxy)-5-methyl-pyridine 
• 315180-15-5 2-fluoro-5-pyridylmethyl chloride 
• 402-69-7 6-fluoropyridine-2-carboxylic acid 
• 123412-44-2 N-<(2-fluoropyridin-5-yl)carbonyl>pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis, radiolabeling and preliminary in vivo evaluation of multimodal radiotracers for PET imaging and targeted radionuclide therapy of pigmented melanoma

Melanin pigment represents an attractive target to address specific treatment to melanoma cells, such as cytotoxic radionuclides. However, less than half of the patients have pigmented metastases. Hence, specific marker is required to stratify this patient population before proceeding with melanin-targeted radionuclide therapy. In such a context, we developed fluorinated analogues of a previously studied melanin-targeting ligand, N-(2-diethylaminoethyl)-6-iodoquinoxaline-2-carboxamide (ICF01012). These latter can be labeled either with 18F or 131I/125I for positron emission tomography imaging (melanin-positive patient selection) and targeted radionuclide therapy purposes. Here we describe the syntheses, radiosyntheses and preclinical evaluations on melanoma-bearing mice model of several iodo- and fluoro(hetero)aromatic derivatives of the ICF01012 scaffold. After preliminary planar gamma scintigraphic and positron emission tomography imaging evaluations, [125I]- and [18F]-N-[2-(diethylamino)ethyl]-4-fluoro-3-iodobenzamides ([125I]4, [18F]4) were found to be chemically and biologically stable with quite similar tumor uptakes at 1 h p.i. (9.7 ± 2.6% ID/g and 6.8 ± 1.9% ID/g, respectively).

Rapid and efficient synthesis of [18F]fluoronicotinamides, [18F]fluoroisonicotinamides and [18F]fluorobenzamides as potential pet radiopharmaceuticals for melanoma imaging

In an attempt to simplify nucleophilic radiofluorination reactions to be amenable for automation, a series of [18F]fluoronicotinamides, [ 18F]fluoroisonicotinamides and [18F]fluorobenzamides were synthesized using one-step

Synthesis and herbicidal activity of 2-cyano-3-(2-fluoro-5-pyridyl) methylaminoacrylates

A series of 2-cyano-3-(2-fluoro-5-pyridyl)methylaminoacrylates were synthesized as herbicidal inhibitors of photosystem II (PSII) electron transport. 2-Fluoro-5-pyridinemethylamine was prepared from 2-amino-5- methylpyridine, subsequent reaction with 2-cyano-3,3-dimethylthioacrylates or 2-cyano-3-methoxyacrylates to yield these title compounds. All of these compounds were confirmed by 1H NMR, IR, mass spectrum and elemental analyses. Their herbicidal activities were evaluated. All of the title compounds showed excellent herbicidal activities to amaranth pigweed and rape in post-emergence treatment. At the rate of 150 g/ha, one compound exhibited similar activity to Cl-analogue. The replacement of chlorine by fluorine group showed the same herbicidal activity.

Bis-acyloxymethyl derivatives

This invention relates to new pyridyl, quinoline and acridine bis-acyloxymethyl compounds; to compositions comprising these compounds; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer in warm-blooded animals. In accordance with this invention, new bis-acyloxymethyl derivatives are provided of the formula: STR1 wherein B is selected from substituted and unsubstituted alkyl, cycloalkyl, aryl, alkenyl, cycloalkenyl and alkynyl; A is selected from hydrogen and B; or, A and B together comprise a pyrrolizine; L is selected from STR2 wherein Y is selected from hydrogen or STR3 each R and Z is independently selected from hydrogen or substituted and unsubstituted alkyl, cycloalkyl, aryl, alkenyl, cycloalkenyl, alkynyl, amine group, each Z' is independently selected from hydrogen and substituted or unsubstituted alkyl; M is Z or is selected from halogen, nitro, hydroxyl, nitrile and substituted or unsubstituted, carboxylic acid group, carboxylic acid ester group, carboxylic acid amide group, sulfonic acid group and sulfonic acid amide group; ether group, thioether group, acylated hydroxyl, sulfonylamide, sulfonylurea, sulfoxide group, sulfone group and mixtures thereof; each n is the same and is 0 or 1; q is from 0-4; and, X is the anion of an acid.

Carboxamidation of pyridines by the system of elemental fluorine- carbonitrile-water: A useful alternative to the chichibabin amination

The title reaction with pyridine, 4-methylpyridine, 3-methylpyridine, 3- bromopyridine, nicotinonitrile, and quinoline yields 2-carboxamido derivatives regioselectively. Isoquinoline is amidated at position 1.

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.

DIRECT FLUORINATION OF SUBSTITUTED PYRIDINES

The direct fluorination of pyridines bearing alkyl, halogen, ester, or ketone functions has been employed to prepare the corresponding 2-fluoro-substituted pyridines.