65836-82-0

Usage

Uses

Used in Pharmaceutical Applications:
1-benzyl-5-methoxy-2,3-dihydro-1H-indol-2-one is used as a potential therapeutic agent for various conditions due to its anti-inflammatory and analgesic properties. It may be beneficial in the treatment of pain and inflammation-related disorders.
Used in Neurological Applications:
1-benzyl-5-methoxy-2,3-dihydro-1H-indol-2-one is used as a potential treatment for psychiatric disorders and neurological conditions, given its neuroprotective properties. It may help alleviate symptoms and improve the quality of life for individuals suffering from such conditions.
Used in Organic Synthesis:
1-benzyl-5-methoxy-2,3-dihydro-1H-indol-2-one is used as a versatile chemical intermediate in organic synthesis, allowing for the development of new compounds with potential applications in various industries.
Used in Medicinal Chemistry Research:
As a compound with potential therapeutic applications, 1-benzyl-5-methoxy-2,3-dihydro-1H-indol-2-one is used in medicinal chemistry research to explore its properties and develop new drugs with improved efficacy and safety profiles.

Upstream product

• 39755-95-8 5-methoxyisatine 
• 16077-10-4 N-benzyl-5-methoxyisatin 
• 100-39-0 benzyl bromide 
• 849092-51-9 N-benzyl-N-(p-methoxyphenyl)-α-ethoxycarbonyl-α-diazoacetamide 
• 1403981-64-5 (E)-2-(2-(benzylideneamino)-5-methoxyphenyl)-N-methyl-N-tosylacetamide 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 38677-50-8 N-benzyl-N-chloroacetyl-p-anisidine 
• 19064-76-7 N-benzylidene-4-methoxyaniline oxide 

Downstream Products

• 1354971-43-9 3-acetyl-1-benzyl-5-methoxy-3-methylindolin-2-one 
• 146919-83-7 1-(1-benzyl-2-hydroxy-5-methoxy-1H-indol-3-yl)ethanone 
• 1247003-79-7 (1R,2S)-2-(3-(4-(4-ethylpiperazin-1-yl)phenyl)-1H-indazol-6-yl)-5'-methoxyspiro[cyclopropane-1,3'-indolin]-2'-one 
• 1247004-41-6 (1R,2S)-5'-methoxy-2-(3-(4-(4-fluoro-1-methylpiperidin-4-yl)phenyl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one 
• 1247002-57-8 (1R,2S)-5'-methoxy-2-(3-(4-piperazin-1-ylphenyl)-1H-indazol-6-yl)spiro(cyclopropane-1,3'-indolin)-2'-one 
• 1247002-41-0 (1R,2S)-5'-methoxy-2-(3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one 

Relevant academic research and scientific papers

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

Enantioselective Synthesis of Multisubstituted Spirocyclopentane Oxindoles Enabled by Pd/Chiral Rh(III) Complex Synergistic Catalysis

An asymmetric [3 + 2]-cycloaddition reaction of α,β-unsaturated 2-acyl imidazoles with spirovinylcyclopropanyl-2-oxindoles catalyzed synergistically by an achiral palladium(0) catalyst and a chiral-at-metal rhodium(III) complex has been developed. A series of biologically important 3-spirocyclopentane-2-oxindoles with four contiguous stereocenters were synthesized in high yields (up to 99%) with excellent stereoselectivities (up to 99% ee, 20:1 dr).

Palladium-catalysed ring-opening [3 + 2]-annulation of spirovinylcyclopropyl oxindole to diastereoselectively access spirooxindoles

A novel palladium-catalysed ring-opening [3 + 2]-annulation of spirovinylcyclopropyl oxindole with α,β-unsaturated nitroalkenes is reported. A series of spirooxindole derivatives were synthesized in high yields and good to excellent diastereoselectivities. This developed protocol offers a new and efficient pathway for the assembly of spirooxindoles.

Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3 + 2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3-Oxindole Derivatives

A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor-acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereoselectivities (up to 20:1 dr).

Synthesis of 3,3-Disubstituted 2-Oxindoles by Deacylative Alkylation of 3-Acetyl-2-oxindoles

An innovative and efficient monoalkylation and nonsymmetrical 3,3-dialkylation of oxindoles has been achieved. First, the monoalkylation of 3-acetyl-2-oxindoles can be performed in good yields under mild reaction conditions using alkyl halides and benzylt

Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence

A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin derivatives is also described.

The discovery of polo-like kinase 4 inhibitors: Identification of (1 R,2 S)-2-(3-((E)-4-(((cis)-2,6-Dimethylmorpholino)methyl)styryl)-1 H -indazol-6-yl)-5′-methoxyspiro[cyclopropane-1,3′-indolin]-2′-one (CFI-400945) as a potent, orally active antitumor agent

Previous publications from our laboratory have introduced novel inhibitors of Polo-like kinase 4 (PLK4), a mitotic kinase identified as a potential target for cancer therapy. The search for potent and selective PLK4 inhibitors yielded (E)-3-((1H-indazol-6-yl)methylene)indolin-2-ones, which were superseded by the bioisosteric 2-(1H-indazol-6-yl)spiro[cyclopropane-1,3′-indolin]-2′-ones, e.g., 3. The later scaffold confers improved drug-like properties and incorporates two stereogenic centers. This work reports the discovery of a novel one-pot double SN2 displacement reaction for the stereoselective installation of the desired asymmetric centers and confirms the stereochemistry of the most potent stereoisomer, e.g., 44. Subsequent work keys on the optimization of the oral exposure of nanomolar PLK4 inhibitors with potent cancer cell growth inhibitory activity. A short list of compounds with superior potency and pharmacokinetic properties in rodents and dogs was studied in mouse models of tumor growth. We conclude with the identification of compound 48 (designated CFI-400945) as a novel clinical candidate for cancer therapy.

Stereoselective intramolecular carbene C-H insertion catalyzed by rhodium(III) porphyrin complexes

Rhodium(III) porphyrin complexes [Rh(Por)Me] are catalytically active towards stereoselective intramolecular carbene C-H insertions of α-diazoacetamides to give cis-β-lactams or trans-γ-lactams in yields up to 99% with regioselectivities up to 100% and ci

Platinum-catalyzed oxoarylations of ynamides with nitrones

A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH 3CN reduction in situ of the initially formed oxoarylation products are also developed.

Ruthenium Catalysts and Uses Thereof

Ruthenium nanoparticles supported on non-cross-linked soluble polystyrene were prepared by reacting [RuCl2(C6H5CO2Et)]2 with polystyrene in open air. They effectively catalyze intra- and intermolecular carbenoid insertion into C—H and N—H bonds, alkene cyclopropanation, and ammonium ylide/[2,3]-sigmatropic rearrangement reactions. This supported ruthenium catalyst is much more reactive than [RuCl2(p-cymene)]2 and Ru(Por)CO] for catalytic intermolecular carbenoid C—H bond insertion into saturated alkanes. By using a-diazoacetamide as a substrate for intramolecular carbenoid C—H insertion, the supported ruthenium catalyst can be to recovered and reused for ten successive iterations without significant loss of activity.