141306-10-7

Usage

Molecular structure

Contains an indole ring with a chloro group at position 6 and a 4-fluorophenyl group at position 3

Fluorinated derivative

Contains a fluorine atom attached to a phenyl ring

Biological activity

Known for diverse biological activities

Potential applications

Medicinal chemistry, agrochemicals, and materials science

Value in synthesis

Unique structure and properties make it a valuable building block for the synthesis of more complex organic molecules.

Upstream product

• 1026987-02-9 6-Chloro-3-(4-fluoro-phenyl)-1H-indole-2-carboxylic acid 
• 17422-33-2 6-chloroindole 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 141306-86-7 methyl 6-chloro-3-(4-fluorophenyl)-1H-indole-2-carboxylate 

Downstream Products

• 141306-16-3 6-chloro-3-(4-fluorophenyl)-1-(4-pyridinyl)-1H-indole 
• 141327-47-1 6-Chloro-3-(4-fluoro-phenyl)-1-piperidin-4-yl-1H-indole 

Relevant academic research and scientific papers

Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands

The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).

A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water

The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

3-ARYLINDOLE COMPOUNDS

3-Arylindole or 3-arylindazole derivatives having formula: STR1 wherein Ar is optionally substituted phenyl or a heteroaromatic group; R. sup.1-R 4 are independently selected from hydrogen, halogen, alkyl, alkoxy, hydroxy, nitro, alkylthio, alkylsulphonyl

Selective, Centrally Acting Serotonin 5-HT2 Antagonists. 2. Substituted 3-(4-Fluorophenyl)-1H-indoles

A series of 3-(4-fluorophenyl)-1H-indoles substituted in the 1-position with 4-piperidinyl, 1,2,3,6-tetrahydro-4-pyridinyl, and 4-piperazinyl was synthesized. By variation of the substituents in the benzene part of the indole nucleus in 1-2-4-3-(4-fluo