13228-37-0

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 13637-43-9 2-methylthioindole 
• 615-43-0 2-iodophenylamine 
• 693-02-7 hex-1-yne 
• 104919-72-4 ethyl N-[2-(1-butynyl)phenyl]carbamate 
• 116491-50-0 2-(hex-1-ynyl)aniline 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 62-53-3 aniline 
• 19591-17-4 o-iodoacetanilide 

Downstream Products

• 1118030-99-1 2-butyl-3-(phenylthio)-1H-indole 
• 1357175-01-9 N-((2-butyl-1H-indol-3-yl)(phenyl)methyl)-4-methylbenzenesulfonamide 
• 1304141-54-5 (2R,3R)-(-)-2-butyl-3-benzylindoline 
• 1304141-55-6 (-)-2-butyl-3-(cyclohexylmethyl)indoline 
• 138459-12-8 4'-(2-Butyl-indol-1-ylmethyl)-biphenyl-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol

Herein, we demonstrated that 2-alkynyldimethylamines easily cyclize in EtOH according to a 5-endo-dig annulation into 2-substituted indoles without the aid of any additives or any metal catalysts to activate the triple bond. Thus, a variety of functionalized 2-styrylindoles, 2-arylindoles, 2-alkynylindoles, and 2-alkylindoles were prepared in high to excellent yields according to an environmentally friendly protocol. The mechanism has been explored to better understand this eco-friendly access to 2-substituted indoles and DFT calculations rationalized the role of the solvent in this N-annulation/dealkylation process.

Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization

By using platinum(II) chloride as a Lewis acid catalyst, concise and efficient syntheses of indole carbamates, 1,2-dihydroisoquinoline carbamates, macrocyclic indole carbamates, indole ureas, and indole phosphoranes have been achieved via tandem Hofmann-t

Gold-catalyzed reactions of 2-alkynyl-phenylamines with α-β-enones

(Chemical Equation Presented) The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/ alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/α,β-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140°C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.

Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF).

The sequential Sonogashira reaction and the cyclization reaction of various 2-iodoanilines and terminal alkynes in the presence of a palladium catalyst and tetrabutylammonium fluoride (TBAF) gave the corresponding 2-substituted indoles in good yields.

Convenient indole synthesis from ethynylanilines with a polymer-supported fluoride

The cyclization reaction of ethynylanilines having phenyl, alkyl, methoxy, cyano, chloro, and ethoxycarbonyl groups with (polystyrylmethyl)trimethylammonium fluoride in dry MeCN under an argon atmosphere at 100°C proceeded in good yields to give the corresponding indoles without affecting these functional groups. Moreover, the polymer-supported fluoride could be reused for the cyclization reaction when the deprotection reaction of the N-substituted indole with the fluoride ion on resin did not occur under the cyclization conditions.

New Synthetic Applications of Water-Soluble Acetate Pd/TPPTS Catalyst Generated in Situ. Evidence for a True Pd(0) Species Intermediate

Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)3 (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65percent).Under the same conditions, the sp2-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99percent).Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling.Furthermore, through a series of kinetic and 31P NMR experiments, we have demonstrated that a mixture of Pd(OAc)2 and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)2(TPPTS)2.A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured.The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition.This complex is considerably less reactive than the corresponding complex generated from PPh3, probably due to steric effects.