95881-82-6

Basic information

• Product Name: 3,3'-Bipyridine, 6,6'-dimethoxy-
• CAS NO: 95881-82-6
• Molecular Formula: C12H12N2O2
• Molecular Weight: 216.239
• Mol File: 95881-82-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,3'-Bipyridine, 6,6'-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Bipyridine, 6,6'-dimethoxy-(95881-82-6)
• EPA Substance Registry System: 3,3'-Bipyridine, 6,6'-dimethoxy-(95881-82-6)

Safety Data

• Hazardous Substances Data: 95881-82-6(Hazardous Substances Data)

Upstream product

• 13472-61-2 5-iodo-2-methoxypyridine 
• 90481-77-9 3-bromo-1-(4-methylbenzenesulfonyl)-1H-indole 
• 15115-52-3 4-bromo-1-phenyl-1H-pyrazole 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 696-62-8 para-iodoanisole 
• 454-79-5 2-Bromo-5-trifluoromethylaniline 
• 163105-89-3 2-methoxy-pyridine-5-boronic acid 
• 5350-93-6 6-Chloro-pyridin-3-ylamine 
• 74-88-4 methyl iodide 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 142929-10-0 <3,3'-Bipyridin>-6,6'-diol 

Relevant articles and documents

Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: Synthesis of highly substituted bipyridines and pyrazinopyridines

(Chemical Equation Presented). A range of halogenated aromatics and heteroaromatics bearing a primary amine group are shown to be suitable substrates for Suzuki cross-coupling reactions with arylboronic acids and pyridylboronic acids under standard conditions, without the need for protection/deprotection steps. New amino-substituted arylpyridines, bipyridines, and pyrazinopyridines have thereby been obtained. Conditions for the efficient syntheses of 2-methoxy-5-pyridylboronic acid 1 and 2-methoxy-3-pyridylboronic acid 2 in ca. 75 g batches have been defined. A 2-fold reaction of 2-amino-5-bromopyrazine with 2,5-dimethoxy-1,4-benzenediboronic acid affords 1,4-dimethoxy-2,5-bis[2-(5-aminopyrazyl)]benzene 31. The X-ray crystal structures of 1 and 31·DMF are reported.

A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)

Efficient introduction of methyl or methyl-d3 into aromatic and heteroaromatic systems still presents a synthetic challenge. In particular, we were in search of a non-cryogenic synthesis of the 5-CD3 version of pirfenidone (4d, also known as Pirespa, Esbriet or Pirfenex), one of the two drugs approved to date for retarding idiopathic pulmonary fibrosis (IPF), a serious, rare and fatal lung disease, with a life expectancy of 3-5 years. The methyl-deuterated version of pirfenidone (4e, also known as SD-560) was designed with the objective of attenuating the rate of drug metabolism, and our goal was to find a green methylation route to avoid the environmental and economic impact of employing alkyllithium at cryogenic temperatures. The examination of several cross-coupling strategies for the introduction of methyl or methyl-d3 into methoxypyridine and pyridone systems culminated in two green and nearly quantitative Suzuki-Miyaura cross-coupling routes in the presence of RuPhos ligand: the first, using commercially available methyl boronic acid or its CD3 analog and the second, employing potassium methyl trifluoroborate or CD3BF3K, the latter obtained by a new route in 88% yield. This led, on a scale of tens of grams, to the synthesis of pirfenidone (4d) and its d3 analog, SD-560 (4e), at 99% isotopic purity.

A convenient synthesis of bipyridines by nickel-phosphine complex-mediated homo coupling of halopyridines

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