19539-50-5

Usage

Uses

Used in Pharmaceutical Industry:
Furo[2,3-c]pyridine is utilized as a key intermediate in the synthesis of pharmaceutical compounds due to its unique structure and reactivity. It contributes to the development of novel drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, Furo[2,3-c]pyridine is employed as a building block for the creation of new agrochemicals. Its structural properties allow for the design of molecules with specific pesticidal or herbicidal activities, enhancing crop protection strategies.
Used in Materials Science:
Furo[2,3-c]pyridine is used as a component in the development of advanced materials. Its incorporation into material structures can lead to the creation of materials with improved properties, such as enhanced stability, conductivity, or specific optical characteristics, depending on the application.
Overall, Furo[2,3-c]pyridine's potential applications span across multiple industries, highlighting its importance as a versatile chemical building block in organic chemistry.

InChI:InChI=1/C7H5NO/c1-3-8-5-7-6(1)2-4-9-7/h1-5H

Upstream product

• 84400-99-7 7-Chlorofuro[2,3-c]pyridine 
• 106531-53-7 2,3-Dihydrofuro<2,3-c>pyridin-3-ol 
• 92404-66-5 3-bromofuro<2,3-c>pyridine 
• 181526-20-5 Furo[2,3-c]pyridine 6-oxide 
• 109-72-8 n-butyllithium 
• 1219101-85-5 2-trimethylsilylfuro[2,3-c]pyridine 
• 289473-47-8 3-acetoxy-4-[2-(trimethylsilyl)ethynyl]pyridine 
• 1219102-40-5 acetic acid 4-bromo-pyridin-3-yl ester 
• 161417-28-3 4-bromo-3-hydroxypyridine 
• 34259-86-4 1-benzenesulfonyl-piperidin-4-one 
• 1334308-13-2 6-benzenesulfonyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridine 
• 1334308-12-1 6-benzenesulfonyl-5,6,7,7a-tetrahydro-4H-furo[2,3-c]pyridin-2-one 
• 1228187-72-1 C₁₅H₁₉NO₄S 
• 1228187-59-4 (1-benzenesulfonyl-1,2,3-6-tetrahydropyridin-4-yl)-acetic acid ethyl ester 

Downstream Products

• 112372-06-2 furo<2,3-c>pyridine-2-carboxaldehyde 
• 142502-97-4 2-phenylthiofuro<2,3-c>pyridine 
• 83431-03-2 4-ethyl-3-hydroxypyridine 
• 142503-06-8 4-ethynyl-3-pyridinol 
• 465519-16-8 4-vinyl-3-pyridinol 
• 10128-71-9 3-hydroxyisonicotinic acid 
• 1219102-22-3 2,7-dichlorofuro[2,3-c]pyridine 
• 84400-99-7 7-Chlorofuro[2,3-c]pyridine 
• 1219101-90-2 furo[2,3-c]pyridin-2-ylphenylmethanol 
• 181526-20-5 Furo[2,3-c]pyridine 6-oxide 
• 153863-91-3 2-aminomethylfuro<2,3-c>pyridine 
• 1415504-57-2 2-{[3-(furo[2,3-c]pyridin-2-yl)imidazo[1-2-b]pyridazin-6-yl](methyl)amino}-1-phenylethanol 
• 112372-15-3 furo<2,3-c>pyridine-2-carboxylic acid 
• 112372-12-0 2-cyanofuro<2,3-c>pyridine 

Relevant academic research and scientific papers

FACTOR XIIA INHIBITORS

This invention relates to compoundsof formula (I)and methods of treatment using the compounds. The invention also relates to processes and methods for producing the compounds of the invention. The compounds of the invention are modulators of Factor XII (e.g. Factor XIIa). In particular, the compounds are inhibitors of Factor XIIa and may be useful as anticoagulants.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

Synthesis of furo[2,3-c]pyridine

A new synthetic strategy toward furo[2,3-c]pyridine (1) starting with N-benzenesulfonylpiperidin-4-one (2) in good yield is described. A synthesis of azasuger analog 9 is also prepared. The Japan Institute of Heterocyclic Chemistry.

Toolbox for regioselective lithiations of furo[2,3-c]pyridine

Chemical Reaction Reprentation A detailed procedure for successive regioselective lithiations of furo[2,3-c]pyridine is described by using n-BuLi and the [n-BuLi/LiDMAE] Superbase. Several polysubstituted furo[2,3-c]pyridines have been efficiently synthesized and some of them were engaged in Pd- or Ni-catalyzed coupling reactions leading to 2,2'- or 7,7'-bifuro[2,3-c]pyridine ligands.

Furopyridines. XXIV [1]. Nitration, Chlorination, Acetoxylation and Cyanation of 2,3-Dihydrofuro[2,3-b]-, -[3,2-b]-, -[2,3-c]- and -[3,2-c]pyridine N-Oxides

Nitration of 2,3-dihydrofuro[3,2-b]- N-oxide 3b and -[2,3-c] pyridine N-oxide 3c afforded the nitropyridine compounds 4b, 5b and 6 from 3b and 4c, 5c, 5′c and 7 from 3c, while -[2,3-b]- N-oxide 3a and -[3,2-c]pyridine N-oxide 3d did not give the nitro compound. Chlorination of 3b and 3c with phosphorus oxychloride yielded mainly the chloropyridine derivatives 15b, 15′b from 3b and 15c and 15′c from 3c, whereas 3a and 3d gave pyridine derivatives formed through fission of the 1-2 ether bond of the furopyridines 13a, 14 and 13d. Acetoxylation of 3b and 3c gave 3-acetoxy derivatives 18b and 18c and the parent compound 1b and 1c. Acetoxylation of 3a yielded compounds formed through fission of the 1-2 bond 16 and 17 and 3d gave furopyridones 19 and 19′. Cyanation of 3b and 3c yielded mainly the cyanopyridine compounds 20b, 20c and 20′c. Cyanation of 3a and 3d gave the cyanopyridine compounds 20a, 20d and 20′d accompanying formation of the pyridine derivatives 21a, 21d and 21′d.

Furopyridines. XXI [1]. Synthesis of Cyano Derivatives of Furo-[2,3-b]-,-[2,3-c]- And -[3,2-c]pyridine and Their Conversion to Derivatives Having Another Carbon-substituent

Cyanation of furo[2,3-b]-, -[2,3-c]- and -[3,2-c]pyridine N-oxides 1a, 1b and 1c by the Reissert-Henze method, reaction with benzoyl chloride and trimethylsilyl cyanide in dichloromethane and the reaction with trimethylsilyl cyanide and triethylamine in acetonitrile afforded 6-cyanofuro[2,3-b]- 2a, 7-cyanofuro[2,3-c]- 2b and 4-cyanofuro[3,2-c]pyridine 2c in moderate to excellent yield. The cyano group in 2a, 2b and 2c was converted to carboxamides 3a, 3b and 3c, ethyl imidates 5a, 5b and 5c and ethyl carboxylates 6a, 6b and 6c. Reaction of the N-oxides with trimethylsily bromide in acetonitrile gave the deoxygenated furopyridine 7a and 7d, bifuropyridyl 8b and 8c, and the N-oxide 9 of 8c.

Furopyridines. XII. Reaction of 3-Bromo, 2-Phenylthio and 2-Phenylthio-3-bromo Derivatives of Furo-, Furo-, Furo- and Furopyridine with Several Alkyllithiums

This paper describes reactions of 3-bromo- 1a-d, 2-phenylthio- 5a-d and 2-phenylthio-3-bromofuropyridines 6a-d with n-butyl-, t-butyl- and methyllithium and lithioacetonitrile.Lithiation of compounds 1a-d with n-butyl- or methyllithium gave the parent furopyridines 2a-d and o-ethynylpyridinols 3a-d.Reaction of compounds 5a-d with methyllithium afforded o-(phenylthioethynyl)pyridinols 7a-d, which were also yielded by reaction of compounds 6a-d with t-butyl- or methyllithium.The phenylthio group in compounds 7a-d were substituted with t-butyl group by the reaction with excess t-butyllithium.In contrast, 2-phenylthio group in compounds 5a-d and 6a-d was substituted with cyanomethyl group by reaction with lithioacetonitrile to give compounds 11a-d and 10b,c respectively.

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.

Furopyridines. I. Synthesis of Furopyridine

The parent framework of furopyridine has been synthesized. 3-Furoic acid chloride (2) was reduced with bis(triphenylphosphine) copper(I) tetrahydroborate to afford 3-furaldehyde (3) which was condensed with malonic acid to give β-(3-furyl)acrylic acid (4).The acrylic acid 4 was converted to the acid azide (5), which in turn was cyclized to give furopyridin-7(6H)-one (6) by heating at 180 deg in diphenylmethane.The pyridone 6 was chlorinated with phosphorus oxychloride, followed by reduction with zinc and acetic acid to give furopyridine (8).