5654-93-3

Usage

InChI:InChI=1/C8H8N2/c1-6-5-10-8-7(6)3-2-4-9-8/h2-5H,1H3,(H,9,10)

Upstream product

• 756531-25-6 N-(3-ethyl-[2]pyridyl)-formamide 
• 1912-42-1 (1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid 
• 10299-67-9 propionaldehyde pyridin-2-ylhydrazone 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 271-63-6 7-Azaindole 
• 67-56-1 methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 149489-03-2 tert-butyl (3-ethylpyridin-2-yl)carbamate 
• 2402-77-9 2,3-dichloro-pyridine 
• 107-11-9 1-amino-2-propene 
• 5654-92-2 7-azagramine 
• 4414-87-3 1H-Pyrrolo[2,3-b]pyridin-3-yl-acetonitrile 
• 138343-75-6 tert-butyl (3-methylpyridin-2-yl)carbamate 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 

Downstream Products

• 464180-73-2 3,7-dimethyl-1H-pyrrolo[2,3-b]pyridine 
• 464180-72-1 1,3-dimethyl-7-azaindole 
• 688782-00-5 3-methyl-1H-pyrrolo[2,3-b]pyridin-7-oxide 
• 145934-57-2 2-chloro-3-methylpyrrolo-[2,3-b]pyridine 

Relevant academic research and scientific papers

Excited-state proton phototransfer in the (3-methyl-7-azaindole)-(7- azaindole) heterodimer

A molecule of 7-azaindole and another of 3-methyl-7-azaindole form a doubly hydrogen bonded heterodimer of Cs symmetry with a first electronic excited state a′ where the electronic excitation is highly localized on one of the molecular halves. Also, because the electronic excitation only increases the acidity of the pyrrole nucleus and the basicity of the pyridine nucleus in one of the two hydrogen bonds, the heterodimer undergoes single rather than double proton transfer.

Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

4-(Benzoimidazol-2-yl)-thiazole Compounds and Related Aza Derivatives

The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4′, R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

4-(BENZOIMIDAZOL-2-YL)-THIAZOLE COMPOUNDS AND RELATED AZA DERIVATIVES

The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4', R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

AZABICYCLO COMPOUND AND SALT THEREOF

It is intended to provide a novel azabicyclo compound which exhibits both HSP90 inhibitory activity and cell proliferation inhibitory effect. Specifically disclosed is a compound represented by the following general formula (I) or a salt thereof: wherein X1 represents CH or N; any one of X2, X3 and X4 represents N, and the others represent CH; any one or two of Y1, Y2, Y3 and Y4 represent C—R4, and the others are the same or different and represent CH or N; R1 represents an optionally substituted monocyclic or bicyclic unsaturated heterocyclic group having 1 to 4 heteroatoms selected from N, S and O; R2 represents an alkyl group having 1 to 6 carbon atoms, or the like; and R3 and R4 represent —CO—R5 or the like.

HYDRAZONE COMPOUNDS AND THEIR USE

The present invention relates to hydrazone compounds of Formula I: (I) and pharmaceutically acceptable salts and stereoisomers thereof, wherein R1, R2, R3, R4, L1, and L2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted indoles

(Chemical Equation Presented) Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme). dba = dibenzylideneacetone, dppf = 1,1′-bis(diphenylphospanyl)ferrocene.

Excited-state double-proton transfer on 3-methyl-7-azaindole in a single crystal: Deuterium isotope/tunneling effect

Unlike 7-azaindole consisting of the tetrameric configuration, 3-methyl-7-azaindole (3MAI) exists solely as intact double hydrogen-bonded dimeric forms in a single crystal. Both steady-state and time-resolved measurements down to 8.0 K reveal remarkable deuterium isotope effects on the rate of excited-state double proton transfer (ESDPT) in the N(1)-deuterated 3MAI (3MAI-d) single crystal. The rates of ESDPT for the 3MAI-d dimer resolved at 150 K are mainly governed by the proton tunneling mechanism. At 12 K, the nearly temperature-independent ESDPT dynamics lead us to qualitatively deduce a barrier height of ～ 1.73 kcal/mol for the 3MAI-d dimer. The results provide an ideal model to investigate the intrinsic ESDPT dynamics for 7-azaindole analogues in which the structural information is well documented.

A convenient method for the preparation of 5-, 6- and 7-azaindoles and their derivatives

The directed ortho lithiation of 2-tert-butoxycarbonylamino-3-methylpyridine (6a) has provided a convenient method for the preparation of 1H-pyrrolo[2,3-b]pyridine (4a, 7-azaindole). This procedure has been used to prepare a range of 3-substituted 2-tert-butoxycarbonylaminopyridines 6, 2- and 3-substituted and 2,3-disubstituted 1H-pyrrolo[2,3-b]pyridines 4 and shown to be of value in the preparation of 1H-pyrrolo[3,2-c]pyridine (15, 5-azaindole) and 1H-pyrrolo[2,3-c]pyridine (18, 6-azaindole) and derivatives.