2380-84-9

Usage

Uses

Used in Organic Synthesis:
7-Hydroxyindole is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a key component in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-Hydroxyindole is used as an intermediate in the synthesis of drugs. Its unique chemical properties enable the development of new medications with potential therapeutic applications.
Used in Agrochemical Industry:
7-Hydroxyindole also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides, that are essential for protecting crops and ensuring food security.
Used in Specialty Chemicals:
7-Hydroxyindole is utilized in the production of specialty chemicals, which are high-value compounds used in specific applications such as dyes, fragrances, and additives for various industries. Its versatility in organic synthesis makes it a valuable asset in this field.

InChI:InChI=1/C8H7NO/c10-7-3-1-2-6-4-5-9-8(6)7/h1-5,9-10H

Upstream product

• 135328-49-3 7-(diphenylmethoxy)indole 
• 111795-92-7 (3-benzyloxy-5-chloro-2-nitrophenyl)acetonitrile 
• 4770-38-1 7-hydroxy-indoline 
• 95-77-2 3,4-dichlorophenol 
• 67810-89-3 benzhydryl-(2-nitro-phenyl)-ether 
• 84639-19-0 7-(benzyloxy)-1-H-indole-2-carboxylic acid 
• 110655-06-6 (3-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 2376879-92-2 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one 
• 642494-37-9 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole 
• 70957-04-9 N-pivaloyl indole 
• 120-72-9 indole 
• 86-74-8 9H-carbazole 
• 3189-22-8 7-methoxy-1H-indole 
• 504-02-9 1,3-cylohexanedione 

Downstream Products

• 5526-13-6 1H-indol-7-yl acetate 
• 944086-12-8 7-isopropoxy-1H-indole 
• 927181-96-2 7-ethoxy-1H-indole 
• 853021-86-0 7-(2-cyanoethoxy)-1H-indole 
• 475576-80-8 2-amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-indolo[7,6-b]pyran 
• 475576-93-3 2-Amino-3-cyano-4-(3-trifluromethyl-phenyl)-4H-indolo[7,6-b]pyran 
• 475576-94-4 2-Amino-3-cyano-4-(5-methyl-pyridin-3-yl)-4H-indolo[7,6-b]pyran 
• 475577-00-5 2-Amino-3-cyano-4-(6-methyl-pyrazin-2-yl)-4H-indolo[7,6-b]pyran 
• 475576-96-6 2-Amino-3-cyano-4-(5-cyano-pyridin-3-yl)-4H-indolo[4,5-b]pyran 
• 313656-45-0 2-(1H-Indol-7-yloxy)-1-ethanol 
• 1206199-62-3 7-methoxymethoxyindole 

Relevant academic research and scientific papers

Palladium-Catalyzed Silacyclization of (Hetero)Arenes with a Tetrasilane Reagent through Twofold C?H Activation

The use of an operationally convenient and stable silicon reagent (octamethyl-1,4-dioxacyclohexasilane, ODCS) for the selective silacyclization of (hetero)arenes via twofold C?H activation is reported. This method is compatible with N-containing heteroarenes such as indoles and carbazoles of varying complexity. The ODCS reagent can also be utilized for silacyclization of other types of substrates, including tertiary phosphines and aryl halides. A series of mechanistic experiments and density functional theory (DFT) calculations were used to investigate the preferred pathway for this twofold C?H activation process.

Rhodium-Catalyzed sp2 C-H Acetoxylation of N-Aryl Azaindoles/N-Heteroaryl Indolines

A silver- and copper-free rhodium-catalyzed C-H acetoxylation reaction of azaindoles has been achieved at near ambient temperature employing PIDA as a nonmetallic acetoxy source. The method is highly selective, efficient, and scalable and requires acetic anhydride as the sole additive. The scope of the reaction has been successfully tested with a wide array of medicinally important heterocyclic scaffolds with diverse functional group tolerance. A series of kinetic experiments was conducted to gain detailed insight into the reaction mechanism. The methodology developed could be successfully expanded for C7-acetoxylation of indoline derivatives using pyrimidine as a detachable directing group for the synthesis of 7-hydroxyindole.

Cu(I)-Catalyzed Site Selective Acyloxylation of Indoline Using O2 as the Sole Oxidant

A Cu(I)-catalyzed regioselective cross-dehydrogenative coupling of indoline with a variety aryl and alkyl carboxylic acids is described. The divergent process for the oxygenation was achieved in satisfactory yields under additive free conditions, which provides an efficient strategy for the regioselective C7 functionalization of indolines using inexpensive copper catalyst. Oxygen as the sole oxidant is required in this protocol. The method is tolerated by a wide range of functional groups. Preliminary mechanistic study provided support for a reversible C?H bond metallation step. (Figure presented.).

DUAL-INHIBITORS OF CELLULAR NECROPTOSIS AND FERROPTOSIS FOR USE IN THE TREATMENT OF ORGAN TRANSPLANT PATIENTS

The invention relates to chemical compounds for use as a medicament in the prevention of organ transplant rejection and/or transplant organ damage. In embodiments of the invention, the compound inhibits and/or reduces ferroptosis and necroptosis of cells of the transplanted organ. In further embodiments, the patient is at risk of transplant rejection and/or is at risk of or shows signs of ischemia-reperfusion injury and/or necroinflammation.

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

Synthetic approach to telomerase inhibitor dictyodendrin B: Synthesis of the pyrrolo[2,3-c]carbazole core

The core structure of the telomerase inhibitor, dictyodendrin B, was synthesized by using the palladium-catalyzed cross-coupling reaction of 3-aryl-1-(2-arylethyl)-4-hydroxy-2,5-bismethoxycarbonylpyrrole triflate with 7-alkoxyindole-3-boronate as the key step.

Novel approaches towards the LTD4/E4 antagonist, LY290154

Several novel approaches have been investigated for the synthesis of the LTD4/E4 antagonist LY290154. Significant improvements to the discovery route were first made by using an indoline nucleophile instead of an indolyl anion in the key substitution step. An alternative approach, introducing the 7-chloroquinoline moiety in the latest stages of the synthesis was then demonstrated. Interestingly, the pivotal intermediate of this latter route was also obtained in a one-pot process following a Katritzky methodology. Finally, an asymmetric synthesis offering significant advantages over the enantioselective route reported by McKillop was demonstrated.

Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles

Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.

Convenient synthesis of 7-hydroxyindole

7-Hydroxyindole, the key building block for the synthesis of AJ-9677 1, was prepared from indoline in six steps in 36% overall yield. AJ-9677 1 is a potent and selective adrenaline β3-agonist being considered as a clinical candidate to treat obesity in those who are suffering from diabetes.

Structure-activity relationship study of novel necroptosis inhibitors

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-α. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.