374818-66-3

Basic information

• Product Name: 5-Iodo-1H-indole, N-BOC protected
• Synonyms: 5-Iodo-1H-indole, N-BOC protected;tert-Butyl 5-iodo-1H-indole-1-carboxylate;5-Iodo-1H-indole, N-BOC protected 97%;1-BOC-5-iodoindole;tert-Butyl 5-iodo-1H-indole-1-carboxylate, 1-(tert-Butoxycarbonyl)-5-iodo-1H-indole;1H-Indole-1-carboxylic acid, 5-iodo-, 1,1-diMethylethyl ester;5-Iodo-1H-indole,N-BOCprotected97%
• CAS NO: 374818-66-3
• Molecular Formula: C₁₃H₁₄INO₂
• Molecular Weight: 343.16023
• Product Categories: blocks;IndolesOxindoles;Iodides
• Mol File: 374818-66-3.mol

Chemical Properties

• Boiling Point: 388.372 °C at 760 mmHg
• Flash Point: 188.681 °C
• Appearance: /
• Density: 1.56 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Iodo-1H-indole, N-BOC protected(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-1H-indole, N-BOC protected(374818-66-3)
• EPA Substance Registry System: 5-Iodo-1H-indole, N-BOC protected(374818-66-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 374818-66-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Iodo-1H-indole, N-BOC protected is used as a building block for the synthesis of various organic compounds. The N-BOC protection allows for selective reactions to occur at other sites on the molecule, facilitating the introduction of specific functionalities.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 5-Iodo-1H-indole, N-BOC protected is used as a key intermediate in the synthesis of drugs. The deprotection of the BOC group reveals the free amine, enabling further reactions that can lead to the formation of bioactive molecules with potential therapeutic applications.
Used in Agrochemical Development:
5-Iodo-1H-indole, N-BOC protected is also utilized in the development of agrochemicals. Its reactivity and the ability to introduce specific functionalities make it a valuable component in the synthesis of compounds with pesticidal or herbicidal properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 5-Iodo-1H-indole, N-BOC protected serves as a valuable research tool. Its versatile reactivity allows for the exploration of new chemical pathways and the development of novel therapeutic agents.
Used in Drug Discovery:
5-Iodo-1H-indole, N-BOC protected is employed in drug discovery processes to identify and optimize potential drug candidates. Its unique properties and reactivity contribute to the design and synthesis of new molecules with therapeutic potential.

InChI:InChI=1/C13H14INO2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,1-3H3

Upstream product

• 16066-91-4 5-iodo-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 913388-48-4 5-(4-methyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester 
• 1206768-17-3 (S)-tert-butyl 5-(1-oxo-1-phenylpropan-2-yl)-1H-indole-1-carboxylate 
• 351500-12-4 tert-butyl 5-(trifluoromethyl)-1H-indole-1-carboxylate 
• 943772-67-6 5-[4-(4-bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester 
• 943772-68-7 5-[2-amino-4-(4-bromo-phenylcarbamoyl)-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester 
• 1259448-21-9 5-(phenylamino)-1H-indole-1-carboxylic acid tert-butyl ester 
• 889108-48-9 5-ethynyl-1H-indole 
• 1613640-01-9 tert-butyl 5-(2-(4-methoxybenzyl)-1,1-dioxidoisothiazolidin-5-yl)-1H-indole-1-carboxylate 

Relevant articles and documents

One-pot access to L-5,6-dihalotryptophans and L-alknyltryptophans using tryptophan synthase

We report, for the first time, the use of tryptophan synthase in the generation of L-dihalotryptophans and L-alkynyltryptophans. These previously unpublished compounds will be useful tools in the generation of probes for chemical biology, in biosynthetic diversification and as convenient building blocks for synthesis.

Mono-selective β-C-H arylation of: N -methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group

2-(Methylthio)aniline (MTA) directed C(sp3)-H functionalisations are efficient and straightforward protocols for the selective β-modification of N-methylated amino acids. The decreased reactivity of MTA in comparison with the 8-aminoquinoline (AQ) directing group allows for selective monoarylations in high yields without the formation of side products. The protocol is also suitable for the introduction of highly functionalised side chains onto the C-terminal alanines of dipeptides. The MTA directing group can easily be removed, providing free carboxylic acids as valuable building blocks.

Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2-H Functionalizations

Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.

Branch-Selective Hydroarylation: Iodoarene-Olefin Cross-Coupling

A combination of cobalt and nickel catalytic cycles enables a highly branch-selective (Markovnikov) olefin hydroarylation. Radical cyclization and ring scission experiments are consistent with hydrogen atom transfer (HAT) generation of a carbon-centered radical that leads to engagement of a nickel cycle.

Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides

By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.

JAK INHIBITOR

A JAK inhibitor comprising, as an active ingredient, a nitrogen-containing heterocyclic compound represented by formula (I) {wherein W represents a nitrogen atom or -CH-; X represents -C (=O) - or -CHR4- (wherein R4 represents a hydrogen atom, or the like); R1 represents the formula described below [wherein Q1 represents-CR8-(wherein R8 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); Q2 represents -NR15- (wherein R15 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); and R5 and R6 may be the same or different and each represents a hydrogen atom, halogen, carboxy, substituted or unsubstituted lower alkyl, or the like], or the like; and R2 and R3 may be the same or different and each represents a hydrogen atom, halogen, substituted or unsubstituted lower alkyl, or the like} or a pharmaceutically acceptable salt thereof.

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus ( HCV ) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, coformulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

Synthesis and evaluation of indolinyl- and indolylphenylacetylenes as PET imaging agents for β-amyloid plaques

Two new phenylacetylene derivatives, 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)indoline 8 and 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole 14, targeting β-amyloid (Aβ) plaques have been prepared. In vitro binding carr

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus ("HCV") or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, co-formulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

Neuroprotective and anti-proliferative compounds

This invention features ring-substituted pyrrolo-β-carboline derivatives and ring-substitution and structural derivatives of 3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione of formulas (I-III), which are useful as neuroprotective and anti-proliferative compounds. Also disclosed are methods for the preparation of these compounds, selected biological profiles and uses of these compounds in the treatment of various neurodegenerative and inflammatory diseases of the human nervous system and in the treatment of various other proliferative disorders characterized by loss of growth or cellular differentiation control including, but not limited to, cancer and inflammation.