68438-39-1

Usage

Derivative of

Indole (a heterocyclic aromatic organic compound)

Structural features

Fluorine group attached to the indole ring
Acetyl group attached to the indole ring

Application

Building block in the synthesis of various pharmaceuticals and other organic compounds

Relevance

Valuable intermediate in organic chemistry

Potential uses

Development of new drugs and compounds with medicinal applications

Upstream product

• 2795-41-7 6-fluoro-1H-indole-3-carbaldehyde 
• 108-24-7 acetic anhydride 
• 2252-51-9 2-choro-4-fluorobenzoic acid 
• 2713-68-0 2-(carboxymethyl-amino)-4-fluoro-benzoic acid 
• 1006-41-3 2-bromo-4-fluorobenzoic acid 
• 3798-90-1 3-acetoxy-1-acetyl-6-fluoro-indole 

Downstream Products

• 1310369-77-7 C₁₉H₂₀BrFN₂O₃S 
• 1310369-83-5 C₁₉H₂₀BrFN₂O₃S 

Relevant academic research and scientific papers

Palladium-catalyzed α-arylation of indolin-3-ones

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.

Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles

3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.

N-heterocyclic carbene-catalyzed enantioselective annulation of indolin-3-ones with bromoenals

N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented. More NHC-organocatalysis: N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented.

Design, synthesis and pharmacological evaluation of conformationally restricted N-arylsulfonyl-3-aminoalkoxy indoles as a potential 5-HT6 receptor ligands

A series of novel conformationally restricted N1-arylsulfonyl-3-aminoalkoxy indoles were designed and synthesized as 5-HT6 receptor (5-HT6R) ligands. Many of the synthesized compounds have moderate in vitro-binding affinities at 5-HT6R. The lead compound 8b (% inhibition=97.2 at 1 μM) from this series has good pharmacokinetic profile in male Wister rats and is active in animal model of cognition like Morris water maze. The details of chemistry, SAR, pharmacokinetics and pharmacological data constitute the subject matter of this report.