341-23-1

Usage

Uses

4-Fluoro-1H-indazole

InChI:InChI=1/C7H5FN2/c8-6-2-1-3-7-5(6)4-9-10-7/h1-4H,(H,9,10)

Upstream product

• 443-86-7 3-fluoro-2-methylaniline 
• 13670-99-0 2,6-difluoroacetophenone 
• 437-81-0 2,6-difluorobenzaldehyde 
• 388-22-7 benzoic acid-(3-fluoro-2-methyl-N-nitroso-anilide) 
• 603-83-8 3-nitro-o-tolylamine 
• 769-10-8 1-fluoro-2-methyl-3-nitrobenzene 

Downstream Products

• 1178903-31-5 4-fluoro-1-(4-methoxybenzyl)-1H-indazole 
• 1178903-42-8 4-fluoro-2-(4-methoxybenzyl)-2H-indazole 
• 518990-32-4 4-fluoro-3-iodo-1H-indazole 
• 1330064-84-0 C₁₃H₁₀FN₃ 
• 1330064-52-2 C₂₁H₁₃ClF₄N₄O 
• 1438463-92-3 C₁₃H₈FN₃O₂ 
• 885521-60-8 3-bromo-4-fluoro-1H-indazole 
• 1561771-60-5 (3-bromo-4-fluoro-1H-indazol-1-yl)(2-chloro-6-(trifluoromethyl)phenyl)methanone 
• 1561949-67-4 ethyl 4-(1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-4-fluoro-1H-indazol-3-yl)-1-methylcyclohex-3-ene-1-carboxylate 
• 1561949-41-4 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)-1-methylcyclohex-3-enecarboxylic acid 
• 1562195-05-4 methyl 4-(1-(2,5-difluorobenzyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoate 
• 1562193-32-1 4-(1-(2,5-difluorobenzyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoic acid 
• 1562195-07-6 methyl 4-(1-(2-bromo-6-(trifluoromethyl)benzyl)-4-fluoro-1H-indazol-3-yl)-5-fluoro-2-methoxybenzoate 
• 1562193-53-6 4-(1-(2-bromo-6-(trifluoromethyl)benzyl)-4-fluoro-1H-indazol-3-yl)-5-fluoro-2-hydroxybenzoic acid 

Relevant academic research and scientific papers

Fluorinated analogues of marsanidine, a highly α2-AR/imidazoline I1 binding site-selective hypotensive agent. Synthesis and biological activities

The aim of these studies was to establish the influence of fluorination of the indazole ring on the pharmacological properties of two selective α2-adrenoceptor (α2-AR) agonists: 1-[(imidazolidin-2-yl)imino]-1H-indazole (marsanidine,

Indazoles: Regioselective protection and subsequent amine coupling reactions

(Chemical Equation Presented) Indazoles are unselectively protected under strongly basic conditions to give a mixture at N-1 and N-2. Under mildly acidic conditions, regioselective protection at N-2 takes place. Thermodynamic conditions lead to regioselective protection at N-1. This trend applies to various substituted indazoles. Protected 5-bromoindazoles participate in Buchwald reactions with a range of amines to generate novel derivatives.

4-Substituted indazoles as new inhibitors of neuronal nitric oxide synthase

A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.

New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine

The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.