78750-82-0

Basic information

• Product Name: 6-methoxy-9H-pyrido[2,3-b]indole
• Synonyms: 6-methoxy-9H-pyrido[2,3-b]indole
• CAS NO: 78750-82-0
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198
• Mol File: 78750-82-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-methoxy-9H-pyrido[2,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-9H-pyrido[2,3-b]indole(78750-82-0)
• EPA Substance Registry System: 6-methoxy-9H-pyrido[2,3-b]indole(78750-82-0)

Safety Data

• Hazardous Substances Data: 78750-82-0(Hazardous Substances Data)

Upstream product

• 2402-77-9 2,3-dichloro-pyridine 
• 104-94-9 4-methoxy-aniline 
• 370571-31-6 3-chloro-N-(4-methoxyphenyl)pyridin-2-amine 
• 1497420-41-3 tert-butyl 5-methoxy-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate 
• 324756-80-1 3-formyl-5-methoxy-indole-1-carboxylic acid tert-butyl ester 
• 10601-19-1 5-methoxyindole-3-carboxaldehyde 
• 52200-48-3 3-bromo-2-chloropyridine 
• 54230-88-5 8-bromotetrazolo[1,5-a]pyridine 

Relevant articles and documents

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes

Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).

Synthesis of α-carbolines starting from 2,3-dichloropyridines and substituted anilines

9H-α-Carbolines have been prepared via consecutive intermolecular Buchwald-Hartwig reaction and Pd-catalyzed intramolecular direct arylation from commercially available 2,3-dichloropyridines and substituted anilines. The combination of a high reaction temperature (180°C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-chloro-N-phenylpyridin-2-amines as no reaction was observed at 120°C and 180°C using different inorganic and other organic bases. On the other hand, nitrogen-methylated pyridine analogues of these substrates {N-[3-chloro-1- methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120°C, with K3PO4 as base, affording the respective 1-methyl-1H-α-carbolines in good yields.