109274-90-0

Basic information

• Product Name: Furo[2,3-b]pyridine, 3-methyl- (9CI)
• Synonyms: Furo[2,3-b]pyridine, 3-methyl- (9CI)
• CAS NO: 109274-90-0
• Molecular Formula: C8H7NO
• Molecular Weight: 133.14728
• Product Categories: PYRIDINE
• Mol File: 109274-90-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Furo[2,3-b]pyridine, 3-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Furo[2,3-b]pyridine, 3-methyl- (9CI)(109274-90-0)
• EPA Substance Registry System: Furo[2,3-b]pyridine, 3-methyl- (9CI)(109274-90-0)

Safety Data

• Hazardous Substances Data: 109274-90-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Furo[2,3-b]pyridine, 3-methyl(9CI) serves as a key building block in the production of various drugs and active pharmaceutical ingredients (APIs). Its distinctive structure and reactivity contribute to its utility in the synthesis of pharmaceuticals and other organic compounds, making it an essential component in the development of novel therapeutic agents.
Used in Organic Synthesis:
Furo[2,3-b]pyridine, 3-methyl(9CI) is utilized as an intermediate in organic synthesis due to its unique structural features. Its reactivity allows for the creation of a wide range of chemical products, making it a versatile component in the synthesis of various organic compounds for different applications.

Upstream product

• 109274-83-1 ethyl 3-hydroxyfuro<2,3-b>pyridine-2-carboxylate 
• 1452-94-4 ethyl 2-chloronicotinate 
• 27038-48-8 furo<2,3-b>pyridin-3(2H)-one 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 372-48-5 2-fluoropyridine 
• 167420-48-6 2-(3-furo<2,3-b>pyridyl)acetic acid 
• 109274-88-6 3-methyl-2,3-dihydrofuro<2,3-b>pyridin-3-ol 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Synthesis of 3-alkylfuropyridines via palladium-catalyzed cyclization of iodopyridinyl allyl ethers

The palladium-catalyzed cyclization of iodopyridinyl allyl ethers derived from dihalopyridines and sodium allyl alkoxide provides furo[2,3-b]-pyridines, furo[3,2-c]pyridines, and furo[2,3-c]pyridines.

Furopyridines. XV. Synthesis and properties of ethyl 2-(3-furo[2,3-b]-, -[3,2-b]-, -[2,3-c]- and -[3,2-c]pyridyl)acetate

Ethyl 2-(3-furopyridyl)acetates 10a-d were synthesized from furopyridin-3(2H)-ones 4a-d by the Wittig-Horner reaction with diethyl cyanomethylphosphonate, hydrolysis and the subsequent esterification. Reaction of compounds 10a-d with lithium diisopropylamide (LDA) gave the corresponding methylene-lithiated intermediate, and the subsequent reaction with benzaldehyde, acetone and iodomethane afforded the methylene-alkylated product respectively, while N,N-dimethylacetamide did not give any reaction product. The 2-position of 10a, b and d is alkylated by the lithiation with excess of LDA and the successive reaction with an electrophile.

Furopyridines. VI. Preparation and Reactions of 2- and 3- Substituted Furopyridines

This paper describes the synthesis and chemical properties of some 2- and 3-substituted furopyridines.Reaction of ethyl 2-chloronicotinate 1 with sodium ethoxycarbonylmethoxide or 1-ethoxycarbonyl-1-ethoxide gave β-keto ester 2 or ketone 5, respectively.Ketonic hydrolysis of 2 afforded ketone 3, from which furopyridine 4 was obtained by the method Sliwa.While, 2-methyl derivative 7 was prepared from 5 by reduction, O-acetylation and the subsequent pyrolysis.Reaction of ketone 3 with methyllithium gave tertiary alcohol 8 which was O-acetylated and pyrolyzed to give 3-methyl derivative 9.Formylation of 4, via lithio intermediate, with DMF yielded 2-formyl derivative 10, from which 7, was obtained by Wolff-Kishner reduction.Dehydration of the oxime 11 of 10 gave 2-cyano derivative 12, which was hydrolyzed to give 2-carboxylic acid 13.Reaction of 3-bromo compound 14 with copper(I)cyanide gave 3-cyano derivative 15.Alkaline hydrolysis of 15 afforded compound 16 and 17, while acidic hydrolysis gave carboxamide 18.Reduction of 15 with DIBAL-H afforded 3-formyl derivative 19.Wolff-Kishner reduction of 19 gave no reduction product 9 but hydrazone 20.Reduction of tosylhydrazone 21 with sodium borohydride in methanol afforded 3-methoxymethylfuropyridine 22.