74420-07-8

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide;3-Nitro-1H-pyrrolo[2,3-b]pyridine 7-oxide;3-Nitro-7-azaindole 7-oxide;7-hydroxy-3-nitropyrrolo[2,3-b]pyridine
• CAS NO: 74420-07-8
• Molecular Formula: C7H5N3O3
• Molecular Weight: 179.13
• Mol File: 74420-07-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 276-277.5 °C (decomp)
• Boiling Point: 463.3 °C at 760 mmHg
• Flash Point: 234 °C
• Appearance: /
• Density: 1.68 g/cm³
• PKA: 9.65±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide(74420-07-8)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide(74420-07-8)

Safety Data

• Hazardous Substances Data: 74420-07-8(Hazardous Substances Data)

Usage

General Description

1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide is a chemical compound that belongs to the pyrrolopyridine family. It has a nitro group and an oxygen atom attached to the seventh carbon of the pyrrolopyridine ring. 1H-Pyrrolo[2,3-b]pyridine, 3-nitro-, 7-oxide is a potent and selective inhibitor of nitric oxide synthesis, making it potentially valuable in the treatment of conditions involving excessive nitric oxide production, such as septic shock and inflammation. Additionally, it may also have applications in the fields of medicinal chemistry and drug discovery for the development of new therapies targeting nitric oxide-related pathways. Further research and development of this compound may lead to the discovery of novel therapeutic agents.

InChI:InChI=1/C7H6N3O3/c11-9-3-1-2-5-6(10(12)13)4-8-7(5)9/h1-4,7-8H/q+1

Upstream product

• 74420-15-8 3-bromo-1H-pyrrolo[2,3-b]pyridine 
• 271-63-6 7-Azaindole 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 74420-18-1 7-Hydroxy-1H-pyrrolo<2,3-b>pyridinium m-chlorobenzoate 
• 74420-08-9 3-Bromo-1H-pyrrolo<2,3-b>pyridine 7-oxide 

Downstream Products

• 918519-53-6 4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Improved synthesis of the selective rho-kinase inhibitor 6-chloro-n4-{3,5-difluoro-4-[(3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl} pyrimidin-2,4-diamine

A highly potent and selective Rho-kinase inhibitor containing a 7-azaindole moiety has been developed at Bayer Schering Pharma. Herein we disclose details of a significantly improved synthesis of the compound in 8.2% overall yield. Key aspects include cost and safety considerations and the uncommon use of a trifluoromethyl group with controllable reactivity as a masked methyl group.

Synthesis of 4-Amino-1H-pyrrolopyridine (1,7-Dideazaadenine) and 1H-Pyrrolopyridin-4-ol (1,7-Dideazahypoxanthine)

4-Amino-1H-pyrrolopyridine (1,7-dideazaadenine) (5) has been synthesized by the iron and acetic acid reduction of 4-nitro-1H-pyrrolopyridine 7-oxide (13), obtained by nitration of 1H-pyrrolopyridine-3-carboxamide 7-oxide (17).Other nitration reactions in the 1H-pyrrolopyridine 7-oxide series are disclosed.The preparation of 1H-pyrrolopyridin-4-ol (1,7-dideazahypoxanthine) (6) began with the hydrolysis of ethyl 1-benzyl-3-cyano-4-oxo-4,7-dihydro-1H-pyrrolopyridine-5-carboxylate (21) to the 3,5-dicarboxylic acid derivative of 1-benzyl-4-oxo-4,7-dihydro-1H-pyrrolopyridine (22).Decarboxylation of 22 with subsequent debenzylation formed 6.