1608124-61-3

Basic information

• Product Name: 1-(pyrimidin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole
• Synonyms: 1-(pyrimidin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole
• CAS NO: 1608124-61-3
• Molecular Weight: 339.32
• Mol File: 1608124-61-3.mol

Chemical Properties

• CAS DataBase Reference: 1-(pyrimidin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(pyrimidin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole(1608124-61-3)
• EPA Substance Registry System: 1-(pyrimidin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1H-indole(1608124-61-3)

Safety Data

• Hazardous Substances Data: 1608124-61-3(Hazardous Substances Data)

Upstream product

• 221044-05-9 N-(2-pyrimidyl)indole 
• 188748-63-2 4-trifluoromethylphenyltriethoxysilane 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 1427669-89-3 (1-(pyrimidin-2-yl)-1H-indol-2-yl)(4-(trifluoromethyl)phenyl)methanone 
• 35692-32-1 trimethoxy(4-(trifluoromethyl)phenyl)silane 
• 120-72-9 indole 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Relevant articles and documents

Cobalt(II)-Catalyzed Oxidative C-H Arylation of Indoles and Boronic Acids

Co(II)-catalyzed C-H C2 selective arylation of indoles with boronic acids through monodentate chelation assistance has been achieved for the first time. The unique features of this methodology include mild reaction conditions, highly C2 regioselectivity, and employment of a Grignard reagent-free catalytic system. A wide range of substrates, including unreactive arenes, are well tolerated, which enables the construction of the coupling products efficiently. This new strategy provides an alternative and versatile approach to construct biaryls using inexpensive cobalt catalyst.

Synthesis method of 2-arylindole derivative

The invention discloses a novel synthesis method of a 2-arylindole derivative. The method comprises the following steps: in an organic solvent, taking an N-(2-pyrimidyl)indole compound and an aryl silane compound as raw materials, taking a catalyst, an oxidizing agent and an activating agent as a catalytic system, carrying out heating and refluxing under stirring, carrying out thin-layer chromatography (TLC) tracking detection until the reaction is complete, and carrying out post-treatment on a reaction solution to obtain the 2-arylindole derivative, wherein the main catalyst is a metal cobaltsalt, the oxidizing agent is copper acetate, and the activating agent is potassium fluoride or cesium fluoride. In the method, cheap metal cobalt is used for catalysis, an oxidative coupling reactionbetween the indole derivative and the aryl silane is realized, and a series of functionalized 2-arylindole compounds are prepared, and the synthesis method of the framework structure is enriched. Simultaneously, the invention provides the novel synthesis method which has low cost, is easy to achieve and is environmentally friendly for synthesis of 2-arylindole compound.

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)-H Bonds Enabled by Cobalt Catalysis

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds

We report here cobalt-N-heterocyclic carbene catalytic systems for the intramolecular decarbonylative coupling through the chelation-assisted C-C bond cleavage of acylindoles and diarylketones. The reaction tolerates a wide range of functional groups such as alkyl, aryl, and heteroaryl groups, giving the decarbonylative products in moderate to excellent yields. This transformation involves the cleavage of two C-C bonds and formation of a new C-C bond without the use of noble metals, thus reinforcing the potential application of decarbonylation as an effective tool for C-C bond formation. This journal is

Ruthenium(II)-Catalyzed Direct C-H Arylation of Indoles with Arylsilanes in Water

The ruthenium(II)-catalyzed, heteroatom-directed C-H arylation of indoles with arylsilanes in water has been developed. The method represents the first example of a ruthenium(II)-catalyzed oxidative C-H arylation in water/aqueous media as a sustainable solvent for C-H functionalization. The reaction enables the synthesis of a wide range of indoles with exquisite selectivity for arylation at the C-2 position. Preliminary mechanistic studies indicate reversibility of the C-H ruthenation step under the developed reaction conditions.

Directed Decarbonylation of Unstrained Aryl Ketones via Nickel-Catalyzed C - C Bond Cleavage

The nickel-catalyzed decarbonylation of unstrained diaryl ketones has been developed. The reaction is catalyzed by a combination of Ni(cod)2 and an electron-rich N-heterocyclic carbene ligand. High functional group tolerance and excellent yields (up to 98%) are observed. This strategy provides an alternative and versatile approach to construct biaryls using an inexpensive nickel catalyst.

Suzuki-Miyaura coupling of unstrained ketones via chelation-assisted C-C bond cleavage

Herein, we report that unstrained ketones can be efficiently employed as electrophiles in Suzuki-Miyaura reactions via catalytic activation of unstrained C-C bonds assist by an N-containing directing group. A wide range of aromatic ketones directly coupled with boronic ester with excellent functional group tolerance. This strategy provides an alternative and versatile approach to constructing biaryls from unstrained ketones.

Rhodium-catalyzed regioselective direct C-H arylation of indoles with aryl boronic acids

A highly efficient Rh(III)-catalyzed direct C-H arylation of indoles with aryl boronic acids under mild conditions has been developed. The methodology features wide substrate scope and excellent functional group compatibility (34 examples, up to 99% yield). The arylated products can also be conveniently transformed into biologically active polycyclic indole derivatives.

Ru-catalysed C-H arylation of indoles and pyrroles with boronic acids: Scope and mechanistic studies

The Ru-catalysed C2-H arylation of indoles and pyrroles by using boronic acids under oxidative conditions is reported. This reaction can be applied to tryptophan derivatives and tolerates a wide range of functional groups on both coupling partners, including bromides and iodides, which can be further derivatised selectively. New indole-based ruthenacyclic complexes are described and investigated as possible intermediates in the reaction. Mechanistic studies suggest the on-cycle intermediates do not possess a para-cymene ligand and that the on-cycle metalation occurs through an electrophilic attack by the Ru centre. High tolerance: An oxidative, Ru-catalysed, and highly selective C-H arylation of indoles and pyrroles is accomplished by using boronic acids (see picture; pym=2-pyrimidyl). The reaction tolerates a wide range of functional groups, including aryl iodides and tryptophan derivatives. New indole-based ruthenacycles are described and their role in the mechanism is investigated.

Rhodium-catalyzed decarbonylative direct C2-arylation of indoles with aryl carboxylic acids

A RhI-catalyzed direct C2-arylation of indoles with diversely substituted aryl carboxylic acids has been developed using 2-pyrimidyl group as an easily installable and readily removable N-directing group. The reaction proceeded smoothly without the need for any external oxidants under relatively mild conditions to produce the C2-arylated indoles in high yields with excellent regioselectivity. A range of functional groups in both coupling partners were tolerated regardless of their electronic properties and positions. With the assistance of the 2-pyrimidyl group, these C2-functionalized products could further undergo C7-arylation to give the C7-aryl indole products. Mechanistic evidence supports that the reaction involves a decarbonylation step, and the carboxylic acids could be activated in situ by treatment with (tBuCO)2O to generate the active anhydrides.