188400-51-3

Upstream product

• 75321-89-0 2-(3-fluorophenyl)acetaldehyde 
• 174609-58-6 1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]-4H-piperazine 
• 862158-41-6 N-(4-[1,2,4]-triazol-4-yl-phenyl)-hydrazinecarboxylic acud tert-butyl ester 
• 862158-39-2 1-but-3-enyl-4-[2-(3-fluoro-phenyl)-ethyl]piperazine 
• 201230-82-2 carbon monoxide 
• 78643-42-2 5-bromopentanal dimethyl acetal 
• 118336-86-0 5-chloro-n-valeraldehyde ethylene acetal 
• 456-48-4 3-Fluorobenzaldehyde 
• 174609-57-5 5-[4-(tert-Butyloxycarbonyl)piperazin-1-yl]pentanal dimethyl acetal 
• 179421-16-0 4-(4-iodo-phenyl)-4H-[1,2,4]triazole 
• 188400-93-3 1-[2-(3-fluorophenyl)ethyl]piperazine 
• 331-25-9 (3-fluorophenyl)acetic acid 
• 540-37-4 p-aminoiodobenzene 
• 25017-13-4 1-(2-bromoethyl)-3-fluorobenzene 

Relevant academic research and scientific papers

Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/fischer indole synthesis

The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

PALLADIUM CATALYZED INDOLIZATION

We have found that 2-unsubstituted indoles of structural formula (IV) can be cost-effectively synthesized in high yield by the palladium-catalyzed coupling/ring closure of a 2-halo or 2-trifluoromethylsulfonyloxy aniline (I) and an acyl silane derivative (II), followed by deprotection of the silyl protecting groups. The process of the present invention is particularly useful to form indoles containing acid-labile substituents such as triazole, acetyl, ketal, cyano, and carbamate, or indoles having a good leaving group in the benzyl position. The advantages of the present process are that it does not require the use of triphenyl phosphine or tetrabutyl ammonium chloride or lithium chloride. When applied to 5-triazolyl substituted indoles, the present process also eliminates the tendency of triazolyl polymerization in the Fischer indole synthesis. Still further, the present invention is also directed to the novel intermediates of structural formulae (V) and (VI).

3-(piperazinylpropyl)indoles: Selective, orally bioavailable h5-HT(1D) receptor agonists as potential antimigraine agents

Clinically effective antimigraine drugs such as Sumatriptan have similar affinity at h5-HT(1D) and h5-HT(1B) receptors. In the search for a h5- HT(1D)-selective agonist as an antimigraine agent, a novel series of 3- (propylpiperazinyl)indoles have been sy

Substituted 1-indolylpropyl-4-phenethylpiperazadine derivatives

A class of 1-?3-(1H-indol-3-yl)propyl!-4-(2-phenylethyl) piperazine derivatives, substituted at the 5-position of the indole nucleus by a five-membered heteroaromatic moiety, and on the phenyl ring of the phenethyl moiety by fluoro, chloro, trifluoromethyl, alkoxy or an oxazolidinone group and optionally by one or two further substituents, are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1D α receptor subtype while possessing at least a 10-fold selective affinity for the 5-HT1D α receptor subtype relative to the 5-HT1D α subtype; they are therefore usefull in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, while eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.