33632-27-8

Usage

Chemical Properties

yellow to beige crystalline powder

InChI:InChI=1/C10H10N2O3/c1-7(13)11-5-4-8-6-9(12(14)15)2-3-10(8)11/h2-3,6H,4-5H2,1H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 
• 108-24-7 acetic anhydride 
• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 
• 75-36-5 acetyl chloride 
• 120-72-9 indole 

Downstream Products

• 5192-03-0 5-amino-1H-indole 
• 4993-96-8 1-(5-aminoindolin-1-yl)ethanone 
• 1612872-74-8 N-(1-acetyl-5-nitroindolin-7-yl)-4-methylbenzenesulfonamide 
• 1187212-54-9 N-((5-nitroindoline)sulfamoyl)benzamide 
• 1187212-51-6 N-((5-aminoindoline)sulfamoyl)benzamide 
• 4770-32-5 1-(5-hydroxy-2,3-dihydroindol-1-yl)ethanone 
• 6146-52-7 5-nitroindole 
• 220442-80-8 1-acetyl-7-bromo-5-nitro-indoline 
• 6019-39-2 N-(1H-indol-5-yl)benzamide 
• 87240-06-0 7-bromo-5-nitroindoline 
• 114144-24-0 1-acetyl-2,3-dihydro-7-bromoindole 
• 15918-80-6 5-amino indoline 
• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 

Relevant academic research and scientific papers

INDOLE DERIVATIVES. 131. THE BASICITY OF 5- AND 6-AMINOINDOLES

The pKa values for the 5- and 6-aminoindoles were determined from potentiometric titration curves and from 13C NMR data on the total change of the chemical shifts of the carbon atom signals on protonation of the amino group.The pKa values obtained (5.99 and 5.53) were higher then those of aniline (3.92) or β-naphthylamine (3.39).

Regioselective C5 nitration of N-protected indolines using ferric nitrate under mild conditions

An efficient and facile process has been developed for the regioselective C5 nitration of the N-protected indolines using ferric nitrate as the nitrating reagents. The reaction proceeded smoothly in moderate to excellent yields with high efficiency and broad substrate scope under mild conditions. In addition, the synthesized nitration products can be further transformed to 5-nitroindolines and C5-nitroindole derivatives. The method is operationally simple, efficient, and might have potential application in industry production.

C5 nitration method of indoline compound

The invention discloses a C5 nitration method of an indoline compound. According to the method, cheap copper salt is used as a catalyst, organic small molecular tert-butyl nitrite (TBN) is used as a metal-free nitro source, and the air is used as an oxidizing agent. The above materials are subjected to C5 C-H functionalization in an organic solvent so as to realize C5 C-H nitration of the indolinecompound and obtain the C5 nitrated indoline compound. The method of the invention has advantages of simple reaction operation, low reaction cost, high yield, mild condition, no heavy metal pollution, etc.

Using weak interactions to control C-H mono-nitration of indolines

An unprecedented C-H mononitration of indolines either at the -C5 or -C7 positions under mild condition is reported here. The roles of multiple weak interactions and factors such as steric factors, electronic effects, cation-π interactions, and solvent polarity were established, and we achieved a 100% regioselective electrophilic aromatic (EArS) nitration using Cu(NO3)2 or AgNO3.

Synthesis method for acylindoline-type compound with C-5 position substituted by nitro group

The invention discloses a synthesis method for an acylindoline-type compound with a C-5 position substituted by a nitro group, wherein a reaction general formula is represented as follows, R referring to alkyl groups including hydrogen (H), 4-methyl and 7-methyl groups. The synthesis method is simple and high-effective, wherein by means of ferric nitrate nonahydrate, the acylindoline-type compound with the C-5 position substituted by a nitro group is produced directly through one step. The reaction has strong zone selectivity and high synthesis efficiency. The raw materials are easy to prepare, and the nitration reagent, ferric nitrate nonahydrate, is low-cost and easy-to-obtained, has wide source and is stable and low-toxic. The reaction is free of protection by inert gas and can be directly carried out in air, has simple operations and gentle conditions, employs a low-cost and easy-to-obtained solvent, and has wide adaptable range of a substrate. The method is low in requirement on reaction conditions, has wide adaptable range, has significant advantages than known methods, and has a potential wide application prospect.

BROMODOMAIN INHIBITOR

The present invention relates to substituted heterocyclic derivative compounds, compositions comprising said compounds, and the use of said compounds and compositions for epigenetic regulation by inhibition of bromodomain-mediated recognition of acetyl lysine regions of proteins, such as histones. Said compositions and methods are useful for the treatment of cancer and neoplastic disease.

Rhodium-catalyzed direct C7 alkynylation of indolines

An efficient rhodium(III)-catalyzed direct C7 alkynylation of indoline C-H bonds with the alkynylated hypervalent iodine reagents has been developed. This reaction proceeds smoothly under mild conditions over a wide structural scope with high site-selectivity and excellent functional-group tolerance. N-Acetyl as well as other N-acyls served as effective directing groups (DG). This procedure allows for the synthesis of a variety of 7-alkynyl-substituted indolines in good to excellent yield. More significantly, C7-alkynylated indoles through further transformations have been successfully accessed.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to pharmaceutical compounds, compositions and methods, especially as they are related to compositions and methods for the treatment and/or prevention of a proliferation disorder, a cancer, a tumor, an inflammatory disease, an autoimmune disease, psoriasis, dry eye or an immunologically related disease, and in some embodiments diseases or disorders related to the dysregulation of kinase such as, but not limited to, EGFR (including HER), Alk, PDGFR, BLK, BMX/ETK, FLT3(D835Y), ITK, TEC, TXK, BTK, or JAK, and the respective pathways.

Ruthenium-catalyzed C7 amidation of indoline C-H bonds with sulfonyl azides

A ruthenium-catalyzed direct C7 amidation of indoline C-H bonds with sulfonyl azides was developed. This procedure allows the synthesis of a variety of 7-amino-substituted indolines, which are useful in pharmaceutical. The good functional tolerances, as well as the mild conditions, are prominent feature of this method.

NOVEL PROTEIN TYROSINE PHOSPHATASE - IB INHIBITORS

The present invention relates to the novel compounds of the general formula (I), wherein the symbols are same as described in specification, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, to process and intermediates for the preparation of the above said compounds, having the utility of these compounds in medicine and to methods for their therapeutic use, and their use in the treatment of metabolic disorders.