171919-36-1

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl- (9CI)
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl- (9CI);1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde;1-Methy-1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde;1-Methyl-1H-Pyrrolo[2,3-B]Pyridine-3-Carbaldehyde(WX624086)
• CAS NO: 171919-36-1
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17262
• EINECS: 604-604-1
• Product Categories: ALDEHYDE
• Mol File: 171919-36-1.mol

Chemical Properties

• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 156.3 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 2.12E-05mmHg at 25°C
• Refractive Index: 1.747
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl- (9CI)(171919-36-1)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl- (9CI)(171919-36-1)

Safety Data

• Hazardous Substances Data: 171919-36-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl(9CI) is used as a starting material for the synthesis of various pharmaceuticals and chemical compounds. Its unique structure allows for the development of new drugs with potential therapeutic effects.
Used in Anticancer Applications:
1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl(9CI) has been studied for its potential as an anticancer agent. Its specific mechanism of action and effectiveness in treating various types of cancer are still under investigation.
Used in Treatment of Inflammatory and Autoimmune Diseases:
1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-methyl(9CI) has also been explored for its potential use in the treatment of inflammatory and autoimmune diseases. Its exact role and efficacy in these conditions are yet to be fully understood and require further research.

InChI:InChI=1/C8H6N2O/c11-5-6-4-10-8-7(6)2-1-3-9-8/h1-5H,(H,9,10)

Upstream product

• 27257-15-4 1-methyl-1H-pyrrolo[2,3-b]pyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 67-68-5 dimethyl sulfoxide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 271-63-6 7-Azaindole 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 
• 616-38-6 carbonic acid dimethyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 171919-37-2 1-methyl-1H-pyrrolo<2,3-b>pyridine-3-carboxylic acid 
• 1094709-34-8 1-methyl-3-[(E)-2-nitrovinyl]-1H-pyrrolo[2,3-b]pyridine 
• 441715-88-4 C₃₀H₃₃FN₄O₅ 
• 441712-69-2 trans-4-[1-[[2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridinyl)]-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 1355338-02-1 6-methoxy-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-phenylquinoline 
• 1198277-81-4 1-methyl-4-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 

Relevant articles and documents

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

I2-mediated C3-formylation of indoles by tertiary amine and H2O

An I2-promoted 3-formylation of free (N-H) and N-substituted indoles with tetramethylethylenediamine (TMEDA) and H2O as the carbonyl source is achieved, providing 3-formylindole in moderate to excellent yields with good functional gr

The ammonium-promoted formylation of indoles by DMSO and H2O

DMSO and H2O is an efficient combination in the NH 4OAc-promoted formylation of indole, where DMSO serves as a C1 carbon source. The mechanism study reveals that the procedure involves a usual and unusual Pummerer reaction.

Identification of trans-4-[1-[[7-fluoro-2-(1-methyl-3-indolyl)-6- benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid as a potent, orally active VLA-4 antagonist

For the purpose of obtaining orally potent VLA-4 inhibitors, we have carried out structural modification of the (N′-phenylureido)phenyl group in compound 1, where the group was found to be attributed to poor pharmacokinetic profile in our previous research. Through modification, we have identified several compounds with both potent in vitro activity and improved oral exposure. In particular, compound 7e with 7-fluoro-2-(1-methyl-1H-indol-3- yl)-1,3-benzoxazolyl group as a novel replacement of the (N′-phenylureido) phenyl group significantly inhibited eosinophil infiltration into bronchoalveolar lavage fluid at 15 mg/kg in an Ascaris-antigen-induced murine bronchial inflammatory model, and its efficacy was comparable to that of the anti-mouse α4 antibody (R1-2).

The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen

A copper-catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The C-H bonds of indoles were C-3-formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3-formylindoles. Copyright

Synthesis and cytotoxicity studies of achiral azaindole-substituted titanocenes

From the reaction of 1-methyl-1 H-pyr-rolo[2,3-b]pyridine (1a),1-(methoxymethyl)-1 H-pyrrolo[2,3-b]pyridine (1b), 1-isopropyl-1 H-pyrrolo[2,3-b]pyridine (1c), and 1-(4-methoxybenzyl)-1 H-pyrrolo[2,3-b] pyridine (1d) under Vilsmeier-Haak conditions, the co

A rapid method toward the synthesis of new substituted tetrahydro α-carbolines and α-carbolines

A rapid and efficient method for stereoselective synthesis of new substituted tetrahydro-α-carbolines using Diels-Alder reaction under microwave irradiation has been developed. Further, dehydrogenation of these adducts resulted in synthesis of new substit

Green N-methylation of electron deficient pyrroles with dimethylcarbonate

The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72-98% yields and is considered to be green chemistry relative to the more common use of methyl halides or dimethyl sulfate.

PIPERAZINYL OXOALKYL TETRAHYDRO-BETA-CARBOLINES AND RELATED ANALOGUES

Piperazinyl oxoalkyl tetrahydro-beta-carbolines and related analogues of the formula (I): are provided, as are methods for their preparation and use. Such compounds may generally be used to modulate ligand binding to histamine H3 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and therapeutic methods are provided, as are methods for using such ligands for detecting histamine H3 receptors (e.g., receptor localization studies).