13472-81-6

Usage

Chemical Properties

beige to light brown crystalline powder

InChI:InChI=1/C5H3Br2NO/c6-3-1-4(7)5(9)8-2-3/h1-2H,(H,8,9)

Upstream product

• 142-08-5 2-Pyridone 
• 35486-42-1 2-amino-3,5-dibromopyridine 
• 680592-71-6 (6-hydroxy-[3]pyridyl)-arsonic acid 
• 142-08-5 2-hydroxypyridin 
• 7647-01-0 hydrogenchloride 
• 39856-50-3 5-bromo2-nitropyridine 
• 504-29-0 2-aminopyridine 
• 13466-43-8 3-bromopyridin-2(1H)-one 
• 100727-17-1 1-phenyl-2-[2]pyridyloxy-ethanone 
• 33245-33-9 3,5-dibromo-2-nitraminopyridine 
• 13472-92-9 C₅H₃BrNO^(1-)*Na⁽¹⁺⁾ 

Downstream Products

• 14529-54-5 3,5-dibromo-1-methyl-1H-pyridin-2-one 
• 40360-47-2 2-chloro-3,5-dibromopyridine 
• 1651890-44-6 5,6’-di(pyridin-3-yl)-5’-methyl-3-((E)-styryl)-2,3’-bipyridine 
• 120491-71-6 3,5-dibromo-1-phenylpyridin-2(1H)-one 
• 130284-00-3 2-(benzyloxy)-3,5-dibromopyridine 
• 910232-70-1 4-[(5-{3-[(4-tert-butylbenzene)amido]-2-methylphenyl}-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino]benzoic acid 
• 910235-66-4 4-{5-[3-(4-tert-butyl-benzoylamino)-2-methylphenyl]-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino}-benzoic acid ethyl ester 
• 910232-68-7 4-tert-butyl-N-(3-{5-[4-(4-hydroxy-piperidine-1-carbonyl)-phenylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-2-methyl-phenyl)-benzamide 

Relevant academic research and scientific papers

Magnesiate-Utilized/Benzyne-Mediated Approach to Indenopyridones from 2-Pyridones: An Attempt to Synthesize the Indenopyridine Core of Haouamine

An efficient, short-staged synthesis of cis-fused indeno[2,1-b]- and indeno[1,2-c]pyridin-2-ones, starting from 2-pyridones, using magnesiates of type R3MgLi as nucleophilic and deprotonation agents, mediated by benzyne generated in situ, under optimized conditions, is described. Following the developed protocol, rare C4a-arylsubstituted indeno[2,1-b]pyridones, resembling the core of haouamine, were obtained. The protocol offering the one-pot synthesis directly from 2-pyridone is also described.

PROCESS FOR PREPARING BTK INHIBITORS

Methods for preparing the Bruton's Tyrosine Kinase ("BTK") inhibitor compound 2- {3'-hydroxymethyl-1-methyl-5-[5-((S)-2-methyl-4-oxetan-3-yl-piperazin-1-yl)-pyridin-2- ylamino]-6-oxo-1,6-dihydro-[3,4']bipyridinyl-2'-yl}-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H- cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one are provided. Methods for preparing tricyclic lactam compounds are also provided.

Development of an Efficient Manufacturing Process for Reversible Bruton's Tyrosine Kinase Inhibitor GDC-0853

Efforts toward the process development of reversible Bruton's tyrosine kinase (BTK) inhibitor GDC-0853 (1) are described. A practical synthesis of GDC-0853 was accomplished via a key highly regioselective Pd-catalyzed C-N coupling of tricyclic lactam 5 with 2,4-dichloronicotinaldehyde (6) to afford the C-N coupling product 3, a Suzuki-Miyaura cross-coupling of intermediate 3 with boronic ester 4 derived from a Pd-catalyzed borylation of tetracyclic bromide 7, to generate penultimate aldehyde intermediate 2 and subsequent aldehyde reduction and recrystallization. Process development of starting materials 5, 6, and 7 is also discussed.

Chiral Hexahalogenated 4,4′-Bipyridines

The preparation of 27 isomers of chiral hexahalogeno-4,4′-bipyridines by means of two complementary methods is described. The first one is convergent and based on the LDA-induced 4,4′-dimerization of trihalopyridines, whereas the second method is divergent and achieved through regioselective halogenation reactions of 4,4′-bipyridine-2,2′-diones. Iodine in 2,2′-positions of the 4,4′-bipyridines was introduced by a copper-catalyzed Finkelstein reaction (Buchwald procedure) performed on 2,2′-dibromo derivatives. Selected compounds of this new family of atropisomeric 4,4′-bipyridines were enantioseparated by high performance liquid chromatography on chiral stationary phases, and the absolute configurations of the separated enantiomers were assigned by using X-ray diffraction analysis. The latter revealed that various halogen bond types are responsible for crystal cohesion.

Mild regioselective halogenation of activated pyridines with N-bromosuccinimide

Regioselective mono and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated derivatives regioselectively and in high yields. Hydroxy and amino pyridines can also be dibrominated in almost quantitative yield with 2 equivalents of NBS.

INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

Halogenation of pyridinols using bis(sym-collidine)iodine(I) and bis(sym-collidine)bromine(I) hexafluorophosphate

Iodination and bromination of pyridinols was achieved by action of the title reagents in methylene chloride.

HALOGENATION AND NITRATION OF 2-PYRIDONES

Halogenation of the 2-pyridones 2 afforded the corresponding mono-di- or tri-halo derivative depending on the conditions of the reaction.Nitration of 2a gave the dinitro-2-pyridone 4k, while nitration of 2c yielded the 3-nitro derivative 4p.Structures were confirmed by spectral data.

SYNTHESES WITH AROMATIC NITRAMINES, VI SUBSTITUENT EFFECT IN THE PHOTOLYTIC REARRANGEMENT OF NITRAMINOPYRIDINES

All isomeric ring-substituted methyl-2-nitraminopyridines, both 3-nitro- and 5-nitro-2-nitraminopyridines, 5-chloro- and 3-carboxy-2-nitraminopyridines, as well as 3,5-dibromo-2-nitraminopyridine were photolyzed in methanol by irradiation with a low-pressure mercury lamp (253.7 nm).Preference was generally noted for the migration of the side-chain nitro group to the vicinal β-position. 3,5-Dibromo-2-nitraminopyridine gave both 2-amino-3,5-dibromopyridine and 3,5-dibromopyridine-2-one.The ratio of the preparative and quantum yields of the two products were 2.5 and 3.0, respectively.

Kinetics and Mechanism of Bromination of 2-Pyridone and Related Derivatives in Aqueous Solution

The tautomeric system 2-pyridone 2-hydroxypyridine (1a 2a) reacts with aqueous bromine via the principal tautomer 1a at pH 6.Attack upon 1a occurs preferentially at the 3 position, whereas reaction upon the anion probably involves major attack at the 5 position.The facile dibromination of 2-pyridone results from the comparable reactivity of the monobromopyridones at pH 4.These conclusions are based upon kinetic and product studies of the bromination of 1a and various derivatives in aqueous solutions at pH 0-8.With respect to their reactivity toward bromine the pyridones behave as substituted phenoxide ions.