177274-67-8

Usage

Molecular Structure

The compound contains an indole ring, which is a tricyclic aromatic system consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Bromomethyl Group

A bromomethyl group is attached to the 2nd position of the indole ring, which can be used as a synthetic handle for the introduction of various functional groups to the molecule.

Phenylsulfonyl Group

The compound has a phenylsulfonyl group attached to the 1st position of the indole ring, which can be used as a protecting group or a directing group in chemical reactions.

Potential Building Block

The compound is a potential building block for the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and materials.

Unique Structure and Reactivity

The unique structure and reactivity of the compound make it a valuable intermediate in organic synthesis and chemical research.

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 98-09-9 benzenesulfonyl chloride 
• 85678-41-7 N-benzenesulphonyl-2-methyl-3-thiophenoxyindole 
• 1496-78-2 3-bromo-2-methyl-1H-indole 
• 177274-66-7 1-phenylsulfonyl-3-bromo-2-methylindole 

Downstream Products

• 565227-63-6 [3-bromo-1-(phenylsulfonyl)indol-2-yl]methanol 
• 697285-17-9 N-[3-bromo-1-phenylsulfonylindol-2-ylmethyl]-4'-isopropylaniline 
• 510732-10-2 N-[3-bromo-1-phenylsulfonylindol-2-ylmethyl]-2'-bromo-4'-methylaniline 
• 697285-16-8 N-[3-bromo-1-phenylsulfonylindol-2-ylmethyl]-N-methylaniline 
• 1150111-72-0 1-phenylsulfonyl-3-bromo-2-(3,4-dimethoxybenzyl)-1H-indole 
• 1372674-51-5 3-bromo-2-(3-bromo-3-phenylallyl)-1-(phenylsulfonyl)-1H-indole 
• 1372674-53-7 3-bromo-2-(3-bromo-3-phenylallyl)-1-(phenylsulfonyl)-1H-indole 
• 1444444-93-2 2-[2-(4-methylphenyl)sulfonylpropyl]-1H-indole-3-carbonitrile 

Relevant academic research and scientific papers

Pd(0)-Catalyzed Intramolecular Heck reaction of 2/3-Aryl(amino)methyl-3/2-bromoindoles: Syntheses of 3,4-Benzo[ c]-β-carbolines, Benzo[4,5]isothiazolo[2,3- a]indole 5,5-Dioxides, and 1,2-Benzo[ a]-γ-carbolines

One-pot synthesis of 3,4-benzo[c]-β-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)2/PPh3-mediated intramolecular Heck coupling using K2CO3 as a base in DMF at 110 °C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-a]indole 5,5-dioxides instead of the expected γ-carbolines. However, synthesis of the expected γ-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-γ-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.

Unusual dimerization of N-protected bromomethylindoles/benzyl bromide with arylmetal halides: generation of indolylmethyl/benzyl radical

A detailed study on the interaction of N-protected bromomethylindoles with various types of aryl/alkyl Grignard is reported. Full experimental details on the mechanism of the unusual dimerization reaction are presented.

Synthesis of N-protected indolaldehydes using modified Hass procedure

A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields.

Unusual dimerization of N-protected bromomethylindoles using phenylmagnesium chloride

A novel dimerization of N-protected bromomethylindoles involving an exchange reaction with phenylmagnesium chloride is reported.

Stille carbonylation of N-protected bromomethylindoles

A variety of N-protected indolylmethylbromides are carbonylated using 5 mol % Pd(PPh3)2Cl2 under Stille conditions in the presence of an alcohol to afford the corresponding methyl/ethyl esters.

A facile preparation of N-protected indolaldehydes using a modified Hass procedure

The preparation of a variety of N-protected indolaldehydes is reported via the reaction of N-protected bromomethylindoles with 2-nitropropane using NaH/DMF.

An efficient preparation of 1-phenylsulfonylindolyl methyl sulfoxides using KF/m-CPBA

A variety of 1-phenylsulfonylindolylmethyl sulfides are selectively oxidized to the corresponding sulfoxides using a hitherto unexplored KF/m-CPBA system. A major advantage is the absence of over-oxidation.

A Facile Synthesis of 3,4-Benzo-β-carbolines

A convenient method for the synthesis 3,4-benzo-β-carbolines (10) from the corresponding N-phenylsulfonyl-3-bromo-N′-arylisogramines (5) via radical mediated cyclization methodology has been reported.

Synthesis of 4-substituted-1,2,3,4-tetrahydro-β-carbolines via intramolecular radical cyclisation and Heck reaction

A convenient method for the synthesis of 4-substituted-β-carbolines from the corresponding N-allylisogramine derivative is reported using intramolecular free radical cyclisation or Heck reaction.