773-91-1

Basic information

• Product Name: 5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE
• Synonyms: AKOS BC-1686;AKOS BBS-00001012;5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE;TIMTEC-BB SBB013309;UKRORGSYN-BB BBV-139171;1H-indole-2,3-dione, 5-fluoro-1-methyl-;5-fluoro-1-methyl-1H-indole-2,3-dione(SALTDATA: FREE);5-fluoro-1-methyl-indole-2,3-dione
• CAS NO: 773-91-1
• Molecular Formula: C₉H₆FNO₂
• Molecular Weight: 179.15
• Mol File: 773-91-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE(773-91-1)
• EPA Substance Registry System: 5-FLUORO-1-METHYL-1H-INDOLE-2,3-DIONE(773-91-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 773-91-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-1-methyl-1H-indole-2,3-dione is used as a key intermediate in the preparation of Polyfluoro substituted Phenylsulfonylindolone compounds. These compounds are synthesized from Phenylsulfonyldifluoroacetate and 5-Fluoro-1-methylisatin through a decarboxylation addition reaction. The resulting Polyfluoro substituted Phenylsulfonylindolone compounds have potential applications in the development of new drugs and therapeutic agents, particularly in the treatment of various diseases and medical conditions.

Upstream product

• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 77-78-1 dimethyl sulfate 
• 403-46-3 4-fluoro-N,N-dimethylaniline 
• 79-37-8 oxalyl dichloride 
• 847550-41-8 5-fluoro-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-methyl-1,3-dihydroindol-2-one 
• 74-88-4 methyl iodide 
• 124958-74-3 1-(5-fluoro-2-(methylamino)phenyl)ethan-1-one 
• 1184953-70-5 N-methyl-2-iodo-4-fluorophenylamine 
• 41192-39-6 2-bromo-N-(4-fluorophenyl)-N-methyl-acetamide 
• 116176-92-2 5-fluoro-1-methyl-1H-indole 
• 131543-46-9 Glyoxal 
• 459-59-6 4-fluoro-N-methylaniline 
• 41192-31-8 5-fluoro-2,3-dihydro-1-methylindol-2-one 
• 351-09-7 N-(4-fluorophenyl)-2-(hydroxyimino) acetamide 

Downstream Products

• 1330787-00-2 5-fluoro-3-hydroxy-1-methyl-3-((phenylamino)methyl)indolin-2-one 
• 1330787-01-3 5-fluoro-3-hydroxy-1-methyl-3-((p-tolylamino)methyl)indolin-2-one 
• 1330787-02-4 5-fluoro-3-((4-fluorophenylamino)methyl)-3-hydroxy-1-methylindolin-2-one 
• 1330787-03-5 3-((4-chlorophenylamino)methyl)-5-fluoro-3-hydroxy-1-methylindolin-2-one 
• 1330787-04-6 3-((4-bromophenylamino)methyl)-5-fluoro-3-hydroxy-1-methylindolin-2-one 
• 1330787-05-7 3-((2-chloro-4-fluorophenylamino)methyl)-5-fluoro-3-hydroxy-1-methylindolin-2-one 
• 1330787-07-9 5-fluoro-3-hydroxy-1-methyl-3-((3-nitrophenylamino)methyl)indolin-2-one 
• 1376615-60-9 C₂₁H₁₆ClFN₂O₄ 
• 1376615-56-3 C₂₃H₂₁FN₂O₄ 
• 1376615-58-5 C₂₃H₂₁FN₂O₆ 
• 1376615-62-1 C₂₁H₁₆BrFN₂O₄ 
• 1376615-57-4 C₂₂H₁₈ClFN₂O₄ 
• 1342468-64-7 5-fluoro-2-(methylamino)benzoic acid 
• 1414857-25-2 C₂₆H₂₁FN₄O₃ 

Relevant articles and documents

Potent 1,2,4-Triazino[5,6 b]indole-3-thioether Inhibitors of the Kanamycin Resistance Enzyme Eis from Mycobacterium tuberculosis

A common cause of resistance to kanamycin (KAN) in tuberculosis is overexpression of the enhanced intracellular survival (Eis) protein. Eis is an acetyltransferase that multiacetylates KAN and other aminoglycosides, rendering them unable to bind the bacterial ribosome. By high-throughput screening, a series of substituted 1,2,4-triazino[5,6b]indole-3-thioether molecules were identified as effective Eis inhibitors. Herein, we purchased 17 and synthesized 22 new compounds, evaluated their potency, and characterized their steady-state kinetics. Four inhibitors were found not only to inhibit Eis in vitro, but also to act as adjuvants of KAN and partially restore KAN sensitivity in a Mycobacterium tuberculosis KAN-resistant strain in which Eis is upregulated. A crystal structure of Eis in complex with a potent inhibitor and CoA shows that the inhibitors bind in the aminoglycoside binding site snugly inserted into a hydrophobic cavity. These inhibitors will undergo preclinical development as novel KAN adjuvant therapies to treat KAN-resistant tuberculosis.

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles

Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. The products from a range of different N-protected and nonprotected isatins were obtained under mild reaction conditions in high yields and enantioselectivities. The unique reactivity of the thioester moiety enabled diverse derivatization and allowed for the straightforward access to a fluorinated analogue of the anticancer agent (S)-YK-4-279, a therapeutically active compound against Ewing's sarcoma.

Direct catalytic synthesis of β-(C3)-substituted pyrroles: A complementary addition to the Paal-Knorr reaction

The synthesis of β-(C3)-functionalized pyrroles is a challenging task and requires a multistep protocol. An operationally simple direct catalytic synthesis of β-substituted pyrroles has been developed. This one-pot multicomponent method combined aqueous succinaldehyde as 1,4-dicarbonyl, primary amines, and isatins to access hydroxyl-oxindole β-tethered pyrroles. Direct synthesis of the β-substituted free NH-pyrrole is the central intensity of this work. DFT-calculations and preliminary mechanism investigation support the possible reaction pathway. This journal is

A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction

A new asymmetric activation strategy for hydrazones as acyl anion equivalents is developed in the bimetallic catalyzed carbonyl-ene reaction of isatins and hydrazones. Under mild conditions, optically active functionalized 3-hydroxy-2-oxindoles were furnished in up to 98% yield with up to 97% enantioselectivity. In this process, formaldehydetert-butylhydrazone which is seldom employed in asymmetric carbonyl-ene reactions accelerated by a metallic catalyst can be activated well by a Br?nsted base. A possible catalytic cycle is proposed.

Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries

Herein, we have developed a strategy of sequential C-H activations of indole to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, which incorporated both alkyne and spiro-units into indole. Gram-scale synthesis and a one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative further offered a powerful tool for the construction of a versatile spiroindole-containing library via click chemistry. This journal is

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives

The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.

Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes

A novel palladium-catalyzed allylic alkylation of oxindoles with cyclopropyl acetylenes has been developed. Various 1,3-diene oxindole framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio-, and stereoselectivities. The reaction exhibited high atom economy and good functional group tolerance.

Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles

Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.

Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters

A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.