10273-88-8

Upstream product

• 3430-17-9 2-bromo-3-picoline 
• 1620-75-3 2-Cyano-6-methylpyridine 
• 131543-46-9 Glyoxal 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 882521-96-2 pyridine-2-boronic acid N-phenyldiethanolamine ester 
• 109-04-6 2-bromo-pyridine 
• 51954-54-2 2-(p-tolylthio)pyridine 

Downstream Products

• 1518913-03-5 C₂₉H₃₁BN₂ 
• 1518913-10-4 C₂₀H₁₉BN₂ 

Relevant academic research and scientific papers

Synthesis of 2,2-Bipyridines via Suzuki-Miyaura Cross-Coupling

For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2′-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2-bipyridines.

Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines

An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.

Rollover-assisted C(sp2)-C(sp3) bond formation

Rollover cyclometalation involves bidentate heterocyclic donors, unusually acting as cyclometalated ligands. The resulting products, possessing a free donor atom, react differently from the classical cyclometalated complexes. Taking advantage of a rollover / retro-rollover reaction sequence, a succession of oxidative addition and reductive elimination in a series of platinum(II) complexes [Pt(N,C)(Me)(PR3)] resulted in a rare C(sp2)-C(sp3) bond formation to give the bidentate nitrogen ligands 3-methyl-2,2′-bipyridine, 3,6-dimethyl-2,2′- bipyridine, and 3-methyl-2-(2′-pyridyl)-quinoline, which were isolated and characterized. The nature of the phosphane PR3 is essential to the outcome of the reaction. This route constitutes a new method for the activation and functionalization of C-H bond in the C(3) position of bidentate heterocyclic compounds, a position usually difficult to functionalize. Rock and rollover! Rare cases of C(sp2)-C(sp3) bond formation from Pt IV cyclometalated complexes are described, through a succession of oxidative addition and reductive elimination reactions, taking advantage of a rollover / retro-rollover sequence (see scheme).

Process for the production of 2-pyridylpyridine derivatives

A process for producing a 2-pyridylpyridine derivative usable as an intermediate for medicines or agricultural chemicals is provided, which does not require expensive metal catalysts, which does not cause environmental problems, and which can be conducted on an industiral scale. The process comprises the step (A) of producing an amidrazone compound from a cyano group-containing heterocyclic compound in water, the step (B) of producing a 1,2,4-triazine compound from the amidrazone compound in water, and the step (C) of producing a 2-pyridylpyridine derivative from the 1,2,4-triazine compound.

Rapid and efficient synthesis of functionalized bipyridines

The Negishi reaction affords a mild and efficient method to convert chloro- and bromo-pyridines into functionalized 2,2′-bi-pyridines using commercially available starting materials. This method also extends to the conversion of dibromopyridines to 5- and 6-bromobipyridines, which are powerful synthons for incorporation into larger supramolecular systems.

PROCESS FOR THE PRODUCTION OF 2-PYRIDYLPYRIDINE DERIVATIVES

A process for producing a 2-pyridylpyridine derivative usable as an intermediate for medicines or agricultural chemicals is provided, which does not require expensive metal catalysts, which does not cause environmental problems, and which can be conducted on an industiral scale. The process comprises the step (A) of producing an amidrazone compound from a cyano group-containing heterocyclic compound in water, the step (B) of producing a 1,2,4-triazine compound from the amidrazone compound in water, and the step (C) of producing a 2-pyridylpyridine derivative from the 1,2,4-triazine compound.