22246-66-8

Usage

Uses

Used in Organic Chemistry Research:
5-Methoxy-2,3-dihydro-isoindol-1-one is utilized as a chemical intermediate for the synthesis of various organic compounds. Its aromaticity and stability make it a valuable building block in the development of new molecules and materials.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 5-Methoxy-2,3-dihydro-isoindol-1-one is used as a key component in the design and synthesis of potential drug candidates. Its versatility allows for the creation of molecules with specific therapeutic properties, targeting a range of medical conditions.
Used in Material Science:
5-Methoxy-2,3-dihydro-isoindol-1-one is employed as a component in the development of advanced materials, such as polymers and composites, that exhibit unique properties. Its incorporation can lead to materials with improved performance in various applications, including electronics and coatings.
Used in Analytical Chemistry:
As a reference compound, 5-Methoxy-2,3-dihydro-isoindol-1-one is used in analytical chemistry for the calibration of instruments and the development of analytical methods. Its distinct chemical properties make it a reliable standard for comparison and measurement.

InChI:InChI=1/C9H9NO2/c1-12-7-3-2-6-5-10-9(11)8(6)4-7/h2-4H,5H2,1H3,(H,10,11)

Upstream product

• 15365-25-0 methyl 2-(bromomethyl)-4-(methyloxy)benzoate 
• 17100-65-1 2-bromo-4-methoxybenzoic acid methyl ester 
• 22246-21-5 2-cyano-4-methoxybenzoic acid methyl ester 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 201230-82-2 carbon monoxide 
• 50727-04-3 4-methoxyphthalimide 
• 788081-99-2 methyl 2-(bromomethyl)-5-methoxy-benzoate 
• 1007455-19-7 2-aminomethyl-5-methoxybenzoic acid methyl ester hydrochloride 
• 22675-83-8 N-(p-methoxybenzyl)-N-tert-butylamine 
• 77250-70-5 N-(2-(4-methoxyphenyl)-2-oxoethyl)picolinamide 
• 1972-28-7 diethylazodicarboxylate 
• 2393-23-9 4-methoxy-benzylamine 
• 116022-18-5 methyl 4-chloro-3-methoxybenzoate 
• 1138220-77-5 methyl 2-bromo-4-chloro-5-methoxybenzoate 

Downstream Products

• 1263311-25-6 C₁₉H₁₉NO₄ 
• 659737-57-2 6-hydroxy-2,3-dihydro-1H-isoindol-1-one 
• 944718-09-6 2,2-Dimethyl-propionic acid 6-methoxy-1-oxo-1,3-dihydro-isoindol-2-ylmethyl ester 
• 950739-11-4 C₁₉H₁₉NO₄ 
• 1023295-45-5 C₂₃H₂₃N₅O₃S 

Relevant academic research and scientific papers

Br?nsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams

Described herein is a novel Br?nsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations.

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.

COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS

This invention relates to compounds of the Formula (I)-(IX):, as defined herein, or a pharmaceutically acceptable salt, solvate or ester thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, aggrecanase, T

Design and Identification of a Novel, Functionally Subtype Selective GABAA Positive Allosteric Modulator (PF-06372865)

The design, optimization, and evaluation of a series of novel imidazopyridazine-based subtype-selective positive allosteric modulators (PAMs) for the GABAA ligand-gated ion channel are described. From a set of initial hits multiple subseries were designed and evaluated based on binding affinity and functional activity. As designing in the desired level of functional selectivity proved difficult, a probability-based assessment was performed to focus the project's efforts on a single subseries that had the greatest odds of delivering the target profile. These efforts ultimately led to the identification of two precandidates from this subseries, which were advanced to preclinical safety studies and subsequently to the identification of the clinical candidate PF-06372865.

Palladium-Catalyzed Direct C-H Carbonylation of Free Primary Benzylamines: A Synthesis of Benzolactams

A protocol for palladium-catalyzed C-H carbonylation of readily available free primary benzylamines using NH2 as the chelating group under an atmospheric pressure of CO has been achieved, providing a general, atom- and step-economic approach to

Tyrosine Kinase Inhibitor And Uses Thereof

Disclosed is a compound of Formula (I) or a pharmaceutically acceptable salt, ester, or solvate thereof, or their stereoisomers, which can be used as tyrosine kinase inhibitor. Also disclosed is a method for preparing the compound, a pharmaceutical composition and a kit comprising the compound, and uses of the compound. The compound can be used as tyrosine kinase inhibitor, or can be used to reduce or inhibit activity of EGFR or mutant thereof, such as EGFR mutant comprising T790M mutation, in a cell, or to treat and/or prevent a disease associated with overactivity of EGFR, such as cancer.

Traceless Directing Group Assisted Cobalt-Catalyzed C?H Carbonylation of Benzylamines

The first example of cobalt-catalyzed C(sp2)?H carbonylation of benzylamines using a traceless directing group is reported, which was successfully applied to the synthesis of N?unprotected iso-indolinones through direct C?H/N?H bonds activation. This protocol tolerates a variety of functional groups and provides a facile and efficient method for the formal synthesis of (+)-garenoxacin. (Figure presented.).

ISOINDOLINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY

The present invention relates to isoindoline derivatives of the formula (I) or a physiologically tolerated salt thereof. The present invention also relates to pharmaceutical compositions comprising such isoindoline derivatives, and the use of such isoindoline derivatives for therapeutic purposes.

Design and synthesis of pyrrolo[3,2- d ]pyrimidine human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors: Exploration of novel back-pocket binders

To develop novel human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) kinase inhibitors, we explored pyrrolo[3,2-d]pyrimidine derivatives bearing bicyclic fused rings designed to fit the back pocket of the HER2/EGFR proteins. Among them, the 1,2-benzisothiazole (42m) ring was selected as a suitable back pocket binder because of its potent HER2/EGFR binding and cell growth inhibitory (GI) activities and pseudoirreversibility (PI) profile as well as good bioavailability (BA). Ultimately, we arrived at our preclinical candidate 51m by optimization of the N-5 side chain to improve CYP inhibition and metabolic stability profiles without a loss of potency (HER2/EGFR inhibitory activity, IC50, 0.98/2.5 nM; and GI activity BT-474 cells, GI50, 2.0 nM). Reflecting the strong in vitro activities, 51m exhibited potent tumor regressive efficacy against both HER2- and EGFR-overexpressing tumor (4-1ST and CAL27) xenograft models in mice at oral doses of 50 mg/kg and 100 mg/kg.

Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products

An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization.