40963-98-2

Basic information

• Product Name: ethyl 5-methoxy-1,2-dimethylindole-3-carboxylate
• Synonyms: ethyl 5-methoxy-1,2-dimethylindole-3-carboxylate
• CAS NO: 40963-98-2
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.28968
• Mol File: 40963-98-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 5-methoxy-1,2-dimethylindole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-methoxy-1,2-dimethylindole-3-carboxylate(40963-98-2)
• EPA Substance Registry System: ethyl 5-methoxy-1,2-dimethylindole-3-carboxylate(40963-98-2)

Safety Data

• Hazardous Substances Data: 40963-98-2(Hazardous Substances Data)

Upstream product

• 15574-49-9 mecarbinate 
• 77-78-1 dimethyl sulfate 
• 7598-91-6 ethyl 5-hydroxy-2-methylindole-3-carboxylate 
• 74-88-4 methyl iodide 
• 110-89-4 piperidine 
• 40963-89-1 ethyl 6-bromo-5-methoxy-1,2-dimethylindole-3-carboxylate 
• 141-97-9 ethyl acetoacetate 
• 65578-36-1 ethyl N-methyl β-aminocrotonate 

Downstream Products

• 17591-06-9 5-methoxy-1,2-dimethyl-1H-indole 
• 105909-93-1 5-methoxy-1,2-dimethyl-indole-3-carboxylic acid 
• 122946-75-2 3,3-diphenyl-8-methoxy-5-methyl-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 122946-88-7 2-(2,2-Diphenyl-vinyl)-5-methoxy-1-methyl-1H-indole-3-carboxylic acid 
• 131475-48-4 5-Methoxy-1-methyl-2-[(E)-2-(2-prop-2-ynyloxy-phenyl)-vinyl]-1H-indole-3-carboxylic acid 
• 122946-86-5 2-(cyclohexylidenemethyl)-5-methoxy-1-methylindole-3-carboxylic acid 
• 122946-71-8 spiro-1',4'-dihydropyrano<4,3-b>indole)> 
• 122946-67-2 2-(1-Hydroxy-cyclohexylmethyl)-5-methoxy-1-methyl-1H-indole-3-carboxylic acid ethyl ester 
• 122946-72-9 8-methoxy-5-methyl-3-phenyl-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 122946-69-4 2-(2-Hydroxy-2-phenyl-ethyl)-5-methoxy-1-methyl-1H-indole-3-carboxylic acid ethyl ester 
• 122946-92-3 5-methoxy-1-methyl-2-(trans-benzylidenemethyl)indole-3-carboxylic acid 
• 122946-73-0 3,5-dimethyl-8-methoxy-3-phenyl-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 52535-62-3 ethyl 1,2-dimethyl-5-methoxy-6-nitroindole-3-carboxylate 
• 52535-61-2 ethyl 1,2-dimethyl-5-methoxy-4-nitroindole-3-carboxylate 

Relevant articles and documents

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

PYRROLOBENZODIAZEPINE PRODRUGS AND ANTIBODY CONJUGATES THEREOF

The invention relates generally to pyrrolobenzodiazepine monomer and dimer prodrugs having a glutathione-activated disulfide prodrug moiety, a DT-diaphorase-activated quinone prodrug moiety or a reactive oxygen species-activated aryl boronic acid or aryl boronic ester prodrug moiety. The invention further relates to pyrrolobenzodiazepine prodrug dimer-antibody conjugates.

1H NMR studies on the reductively triggered release of heterocyclic and steroid drugs from 4,7-dioxoindole-3-methyl prodrugs

Hypoxia is a feature of several disease states, including cancer and rheumatoid arthritis. Prodrug systems which, after bioreduction, selectively release active drugs in these tissues may be important in therapy. An improved preparation of 1,2-dimethyl-3-hydroxymethyl-5-methoxyindole-4,7-dione was developed. Mitsunobu coupling with (5-substituted) isoquinolin-1-ones (potent inhibitors of poly(ADP-ribose)polymerase) gave 1-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethoxy)isoquinolines and N-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethyl)isoquinolin-1-ones. Similar coupling with the anticancer drug pentamethylmelamine gave its potential prodrug 1,2-dimethyl-3-(N-(4,6-bis(dimethylamino)-1,3,5-triazin-2-yl)-N- methylaminomethyl)-5-methoxyindole-4,7-dione. Treatment of sodium prednisolone hemisuccinate with 3-chloromethyl-1,2-dimethyl-5-methoxyindole-4,7-dione gave an analogous candidate prodrug of the anti-inflammatory drug prednisolone. In a chemical model system for bioreduction, SnCl2 in CDCl3/CD3OD triggered rapid stoichiometric release of isoquinolin-1-ones from the O-linked prodrugs but not from the N-linked analogues. Use of this system allowed the release process to be monitored in situ by 1H NMR spectroscopy. Diethyl hydrazine-1,2-dicarboxylate was found to reduce SnIV to SnII, making the overall reductive release catalytic in tin. The reduced (hydroquinone) prodrug may have a short lifetime under these reductive conditions, meaning that only good leaving groups are expelled. Thus 1-(1,2-dimethyl-4,7-dioxo-5-methoxyindol-3-ylmethoxy)isoquinolines and analogues may be useful as reductively triggered prodrugs.