106531-57-1

Basic information

• Product Name: Furo[2,3-c]pyridine, 3-methyl- (9CI)
• Synonyms: Furo[2,3-c]pyridine, 3-methyl- (9CI)
• CAS NO: 106531-57-1
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.14728
• Product Categories: PYRIDINE
• Mol File: 106531-57-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Furo[2,3-c]pyridine, 3-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Furo[2,3-c]pyridine, 3-methyl- (9CI)(106531-57-1)
• EPA Substance Registry System: Furo[2,3-c]pyridine, 3-methyl- (9CI)(106531-57-1)

Safety Data

• Hazardous Substances Data: 106531-57-1(Hazardous Substances Data)

Upstream product

• 167420-50-0 2-(3-furo<2,3-c>pyridyl)acetic acid 
• 372-47-4 3-Fluoropyridine 
• 22282-75-3 3-fluoro-4-iodopyridine 
• 30152-05-7 1-(3-hydroxypyridin-4-yl)ethan-1-one 
• 106531-56-0 Ethyl 2-(4-Acetyl-3-pyridyloxy)acetate 

Relevant articles and documents

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.

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. V. A Simple Synthesis of Furopyridine and Its 2- and 3-Methyl Derivatives

A simple synthesis of furopyridine and its 2- and 3-methyl derivatives from ethyl 3-hydroxyisonicotinate (2) is described.The hydroxy ester 2 was O-alkylated with ethyl bromoacetate or ethyl 2-bromopropionate to give the diester 3a or 3b.Cyclization of compound 3a afforded ethyl 3-hydroxyfuropyridine-2-carboxylate (4) which was hydrolyzed and decarboxylated to give furopyridin-3(2H)-one (5a).Cyclization of 3b gave the 2-methyl derivative 5b.Reduction of 5a and 5b with sodium borohydride yielded the corresponding hydroxy derivative 6a and 6b, respectively, which were dehydrated with phosphoric acid to give furopyridine (7a) and its 2-methyl derivative 7b. 4-Acetylpyridin-3-ol (8) was O-alkylated with ethyl bromoacetate to give ethyl 2-(4-acetyl-3-pyridyloxy)acetate (9).Saponification of compound 9, and the subsequent intramolecular Perkin reaction gave 3-methylfuropyridine (10).Cyclization of 9 with sodium ethoxide gave 3-methylfuropyridine-2-carboxylic acid, which in turn was decarboxylated to give compound 10.