13228-36-9

Usage

Uses

Used in Medicinal Chemistry:
5-METHYL-2-PHENYLINDOLE is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Material Science:
In the field of material science, 5-METHYL-2-PHENYLINDOLE is utilized as a building block for the creation of novel materials with specific properties. Its structural features and reactivity contribute to the design and synthesis of advanced materials with potential applications in various industries.
Used in Organic Synthesis:
5-METHYL-2-PHENYLINDOLE serves as a versatile reactant in organic synthesis, enabling the formation of a wide range of organic compounds. Its presence in the synthesis process allows for the creation of complex molecules with diverse applications in various fields, including pharmaceuticals, agrochemicals, and specialty chemicals.

InChI:InChI=1/C15H13N/c1-11-7-8-14-13(9-11)10-15(16-14)12-5-3-2-4-6-12/h2-10,16H,1H3

Upstream product

• 4831-18-9 N-phenacyl-p-toluidine 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 93-89-0 benzoic acid ethyl ester 
• 109463-71-0 N-TMS-2,4-Dimethylaniline 
• 104683-04-7 1-(5-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 98-86-2 acetophenone 
• 539-44-6 N-4-methylphenylhydrazine 
• 583-68-6 2-bromo-p-toluidine 
• 98-81-7 1-bromovinylbenzene 
• 1131890-84-0 1-tert-butyl-5-methyl-2-phenyl-1H-indole 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 25109-04-0 1-(p-tolyl)-1,2,3,4-tetrazole 
• 932-87-6 1-Bromo-2-phenylacetylene 

Downstream Products

• 132554-35-9 N-methyl-2-phenyl-5-methylindole 
• 23746-97-6 5-methyl-2-phenyl-indol-3-one oxime 
• 59490-95-8 2-benzamido-5-methylbenzoic acid 
• 23751-25-9 5-methyl-2-phenyl-indol-3-one 
• 117039-85-7 6-methyl-2-phenyl-4H-benzo[d][1,3]oxazin-4-one 
• 21419-51-2 6-methyl-2-phenylquinazolin-4(3H)-one 
• 108618-97-9 N-(2-cyano-4-methylphenyl)benzonitrile 
• 1331947-76-2 5-methyl-1-nitroso-2-phenylindoline 
• 1331947-77-3 5-methyl-2-phenyl-N-(propan-2-ylidene)indolin-1-amine 
• 1331944-17-2 C₂₁H₂₂N₂ 
• 1143571-00-9 (-)-(S)-2-(5-methyl-2-phenyl)indole 
• 1610423-37-4 C₂₂H₂₆N₂O₂ 
• 1610423-22-7 C₁₇H₁₅NO₂ 
• 1610423-33-0 C₁₈H₁₇NO₂ 

Relevant academic research and scientific papers

Iron-palladium association in the preparation of indoles and one-pot synthesis of bis(indolyl)methanes

Indoles were prepared by annulation of the parent alkynylanilines with the use of a new FeCl3-PdCl2 catalytic combination. High yields were obtained by using low loadings of the transition-metal complex (FeCl3-PdCl2: 2 and 1 mol-%, respectively). One-pot accesses to bis(indolyl)methanes and trisubstituted indoles through annulation/Friedel-Crafts alkylation and annulation/1,4-Michael addition sequences, in which FeCl3 acts both as a cooxidant and a Lewis acid are described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of 2-substituted indoles via Pd/C-catalyzed reaction in water

A general and one-pot synthesis of 2-alkyl/aryl substituted indoles via a tandem Pd/C mediated coupling/5-endo-dig cyclization of terminal alkynes (including acetylenic carbinols) with o-iodoanilides in water is reported. The reaction is carried out using PPh3 and CuI as co-catalysts and 2-aminoethanol as a base. The reaction appears to tolerate a variety of functional groups present in the alkynes and does not require the use of any organic co-solvent.

Characterization of heterogeneous aryl-Pd(ii)-oxo clusters as active species for C-H arylation

C-H arylation with heterogeneous palladium was investigated. The surface oxidation of Pd nanoparticles with a hypervalent iodine reagent, [Ph2I]BF4, resulted in the generation of Pd(ii)-aryl-oxo clusters, which were characterized as the crucial intermediate.

One-pot 2-aryl/vinylindole synthesis consisting of a ruthenium-catalyzed hydroamination and a palladium-catalyzed heck reaction using 2-chloroaniline

A one-pot synthesis of 2-aryl- and 2-vinylindoles based on a ruthenium-catalyzed hydroamination and a palladium-catalyzed intramolecular Heck reaction is reported. The ruthenium-catalyzed addition reaction was applied to terminal as well as internal alkynes. Intramolecular Heck reactions of the resulting 2-chloroanilino enamines were achieved using an in situ generated palladium complex derived from an N-heterocyclic carbene. Georg Thieme Verlag Stuttgart.

Palladium-Catalyzed C2?H Arylation of Unprotected (N?H)-Indoles “On Water” Using Primary Diamantyl Phosphine Oxides as a Class of Primary Phosphine Oxide Ligands

We present the Pd-catalyzed arylation of (N?H)-indoles with functionalized haloarenes “on water” using hitherto untested primary diamantyl phosphine oxides (PPO) as ligands. Remarkable C2?H arylation selectivity was achieved by employing functionalized iodoarenes and N-unprotected indoles. We provide evidence that the in situ generated oxide of (9-hydroxydiamant-4-yl)phosphine L1 is key for the reaction efficiency by comparing a set of diamantane-based compounds structurally related to L1. Our results demonstrate the power of the new PPO ligands for the C?H functionalization of unprotected (N?H)-heterocycles.

InBr3-catalyzed intramolecular cyclization of 2-alkynylanilines leading to polysubstituted indole and its application to one-pot synthesis of an amino acid precursor

We describe InBr3-catalyzed cyclization of 2-alkynylaniline derivatives having a variety of functional groups producing polysubstituted indoles. This methodology could be applied to the one-pot synthesis of an amino acid precursor by the addition of a catalytic amount of the indium salt, an imine, and TMSCl.

Stereoselective synthesis of 3-spiropiperidino indolenines via SN2-type ring opening of activated aziridines with 1H-indoles/Pd-catalyzed spirocyclization with propargyl carbonates

3-Spiropiperidino indolenines have been synthesized via novel Lewis acid-catalyzed SN2-type ring opening of activated aziridines with 1H-indoles followed by Pd-catalyzed dearomative spirocyclization with propargyl carbonates in up to 88% yields

One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones

A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.