24621-70-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-INDOL-2-YLMETHANOL is used as a reactant for the synthesis of various pharmaceutical compounds, including:
1. Oxazino[4,3-a]indoles: These are a class of fused indole derivatives with potential applications in the development of new drugs targeting specific biological receptors.
2. 2-arylsulfonylmethyl-3-piperazinylmethylindole derivatives: These compounds serve as 5-HT6 receptor ligands, which can be utilized in the treatment of various neurological and psychiatric disorders by modulating serotonin signaling.
3. SR13668: 1H-INDOL-2-YLMETHANOL is designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol, which is known to block Akt signaling, a crucial pathway in cancer cell survival and proliferation.
4. Azidoand isothiocyanato-substituted indoles: These compounds act as melatoninergic agents, potentially influencing the melatonin system, which is involved in the regulation of sleep-wake cycles, mood, and other physiological processes.

InChI:InChI=1/C9H9NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-5,10-11H,6H2

Upstream product

• 3289-87-0 1-methoxyindole-2-carboxaldehyde 
• 107-19-7 propargyl alcohol 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 144393-28-2 1-methoxymethoxyindole-2-carboxaldehyde 
• 174418-78-1 1,2,3,4-tetrahydropyrazino[1,2-a]indole-1,4-dione 
• 148564-88-9 2,2,2-trifluoro-N-(2-(3-hydroxyprop-1-ynyl)phenyl)acetamide 
• 109-89-7 diethylamine 
• 86531-02-4 1H-indol-1-yl benzoate 
• 3289-82-5 1-hydroxyindole 
• 144219-54-5 1-methoxymethoxyindole 
• 134792-59-9 1-(t-butyldimethylsilyloxy)indole 
• 58881-41-7 6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione 

Downstream Products

• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 143232-23-9 2-phenylthiomethyl-1H-indole 
• 120-72-9 indole 
• 127280-18-6 N-Benzoylindole-2-carboxaldehyde N,N-dimethylhydrazone 
• 107772-42-9 indole-2-carbaldehyde-(2,4-dinitro-phenylhydrazone) 
• 114648-66-7 (1H-indol-3-yl)-(1H-indol-2-yl)-methane 
• 1373438-80-2 (E)-N'-[(1H-indol-2-yl)methylene]-5-bromo-2-methoxybenzohydrazide 
• 1373438-08-4 (E)-N'-((1H-indol-2-yl)methylene)-5-bromo-2-hydroxybenzohydrazide 
• 33553-29-6 1,2,4-triphenyl-9H-carbazole 
• 1616101-34-8 1,2-diphenyl-4-p-tolyl-9H-carbazole 
• 1616101-35-9 4-(4-methoxyphenyl)-1,2-diphenyl-9H-carbazole 
• 1616101-36-0 4-(3-chlorophenyl)-1,2-diphenyl-9H-carbazole 
• 1616101-37-1 4-(4-chlorophenyl)-1,2-diphenyl-9H-carbazole 
• 1616101-38-2 4-phenyl-1,2-di(p-tolyl)-9H-carbazole 

Relevant academic research and scientific papers

Lithiation of 1-alkoxyindole derivatives

Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.

Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu

Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficie

Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols and amines

A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.

Synthesis of indoles: Tetrahydropyrazino[1,2-a]indole-1,4-dione and pyrazino[1,2-a]indole-6,13-diones from piperazine-2,5-diones

The readily available piperazine-2,5-dione has been used to prepare both 1:1 (1-3), with stereotopic methylene protons; and 2:1 (4-6) arylmethylenepiperazine-2,5-diones in above average yields. The halo-derivatives, 1, 4 and 5 were cyclized to pyrazino[1,2-a]indoles, 7-9, using copper bronze. Indole compounds 7 and 9 were further treated, separately, with lithium aluminium hydride, sodium borohydride, lithium hydroxide monohydrate and butyl lithium to yield 2-substituted indoles 10-13.

Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones

o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.

Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols

A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.

A REGIOSELECTIVE LITHIATION OF 1-METHOXYMETHOXYINDOLE AT THE 2-POSITION AND ITS APPLICATION FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES

A regioselective lithiation of 1-methoxymethoxyindole at the 2-position was achieved with n-BuLi at 0 deg C.Subsequent treatment with electrophiles afforded 2-substituted 1-methoxymethoxyindoles, which were readily converted to 2-substituted indoles.

PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES

An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.