86847-74-7

Basic information

• Product Name: 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE
• Synonyms: 2-(TERT-BUTYL)-7-AZAINDOLE;2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE;1H-Pyrrolo[2,3-b]pyridine, 2-(1,1-dimethylethyl)-
• CAS NO: 86847-74-7
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• Mol File: 86847-74-7.mol

Chemical Properties

• Boiling Point: 304.3°Cat760mmHg
• Flash Point: 127.8°C
• Appearance: /
• Density: 1.076g/cm³
• Vapor Pressure: 0.00159mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE(86847-74-7)
• EPA Substance Registry System: 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE(86847-74-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 86847-74-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE is used as a key intermediate in the synthesis of pharmaceutical compounds due to its potential biological activities. Its unique structure allows for the development of new drugs with novel mechanisms of action.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE serves as a valuable building block for the creation of complex organic molecules. Its reactivity, influenced by the steric hindrance of the tert-butyl group, can be harnessed to form a variety of chemical products.
Used in Material Science:
2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE may also find applications in material science, where its structural features could contribute to the development of new materials with specific properties, such as improved stability or novel electronic characteristics.
Further research is necessary to explore the full potential of 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE across various industries and to understand its role in the creation of innovative products and therapies.

InChI:InChI=1/C11H14N2/c1-11(2,3)9-7-8-5-4-6-12-10(8)13-9/h4-7H,1-3H3,(H,12,13)

Upstream product

• 630-18-2 tert-butyl isocyanide 
• 108-99-6 3-Methylpyridine 
• 113975-39-6 2,2-dimethyl-N-<3-(3,3-dimethyl-2-oxobutyl)-2-pyridinyl>propanamide 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 138343-75-6 tert-butyl (3-methylpyridin-2-yl)carbamate 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 13534-99-1 2-Amino-3-bromopyridine 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 3282-30-2 pivaloyl chloride 
• 504-29-0 2-aminopyridine 
• 113975-31-8 N-(3-iodopyridin-2-yl)-2,2-dimethylpropionamide 
• 86847-59-8 2-(pivaloylamino)pyridine 
• 24331-71-3 N,N-dimethylpivalamide 

Downstream Products

• 1014613-61-6 4-bromo-2-(1,1-dimethylethyl)-1H-pyrrolo[2,3-b]pyridine 
• 1312891-51-2 (E)-3-(4-{[2-(2-tert-butyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethylamino]methyl}phenyl)-N-hydroxyacrylamide 
• 1312891-89-6 (E)-3-(4-{[2-(2-tert-butyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethylamino]methyl}phenyl)acrylic acid methyl ester 
• 1049676-91-6 2-tert-butyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 

Relevant articles and documents

AZAINDOLES AND METHODS OF USE THEREOF

Disclosed are compounds according to Formula (I) or (II), and pharmaceutical compositions comprising them. Also disclosed are therapeutic methods, e.g., of treating kidney diseases, using the compounds of Formula (I) or (II). (Formulae (I, (II))

Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO

The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is

Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree of pharmacophore homology between these two targets was discovered. This similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

One-pot synthesis of azaindoles via palladium-catalyzed α-heteroarylation of ketone enolates

(Figure presented) A convenient, one-pot method for the construction of a variety of azaindoles using simple ketones and haloaminopyridines is described.

NOVEL COMPOUNDS

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds according to formula (I) and salts thereof. The compounds of the invention are inhibitors of kinase activity, in particular IKK2 activity.

Reactions of β-(lithiomethyl)azines with nitriles as a route to pyrrolo-pyridines, - quinolines, -pyrazines, - quinoxalines and -pyrimidines

Deprotonation of 3-methylazines, followed by reaction with benzonitile, gives an intermediate which, on treatment with additional strong base, cyclises to give 2-phenyl[1H]-pyrrolo[2,3-b]pyridine. The application of this type of reaction to a variety of n

Metalation/SRN1 Coupling in Heterocyclic Synthesis. A Convenient Methodology for Ring Functionalization

Lithiation, iodination, and fluorine substitution on 2-fluoropyridine gave 2-substituted 3-iodopyridines, which were further subjected to iodine SRN1 substitution by carbon, sulfur, and phosphorus nucleophiles.Iodine substitution by enolates on 2-amino-3-iodopyridines afforded ketones, which were further cyclized to various 1,2-disubstituted pyrrolopyridines. 2-Amino-3-iodo-, 3-amino-4-iodo, and 4-amino-3-iodopyridines were prepared by directed metalation of 2-, 3-, and 4-(pivaloylamino)pyridines.Substitution of iodine by enolates under SRN1 conditions and acidic cyclization led to various 2-substituted pyrrolo, --, and -pyridines in high yields.

Regiospecific Electrophilic Substitution of Aminopyridines: Ortho Lithiation of 2-, 3-, and 4-(Pivaloylamino)pyridines

2- and 4-(pivaloylamino)pyridines have been shown to undergo metalation exclusively at C-3 and these smoothly react with a variety of electrophiles to produce 2,3- and 3,4-disubstituted pyridines, respectively.Removal of the pivaloyl protecting group results in overall electrophilic substitution of an aminopyridine.Utilization of this method is exemplified by efficient syntheses of 2- and 4-aminonicotinaldehydes.Minor modifications of the reaction conditions permitted exclusive ortho metalation of 2-(pivaloylamino)pyridines additionally functionalized by chloro, fluoro, or methyl groups.Although the major product from reaction of 3-(pivaloylamino)pyridine by this method was metalation at C-4, the reaction was complicated by substantial quantities of product derived from nucleophilic attack by n-butyllithium on the pyridine nucleus.