58084-22-3

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 593-51-1 methylamine hydrochloride 
• 615-37-2 ortho-methylphenyl iodide 
• 88070-48-8 N-methylbenzamide 
• 88-67-5 2-Iodobenzoic acid 
• 74-89-5 methylamine 

Downstream Products

• 110166-72-8 2-(2'-phenylethynyl)-N-methyl benzamide 
• 198897-10-8 5-Methoxy-2-(2-methylcarbamoyl-phenylsulfanyl)-benzoic acid 
• 198897-07-3 5-Chloro-2-(2-methylcarbamoyl-phenylsulfanyl)-benzoic acid 
• 293744-63-5 N-Methyl-2-naphthalen-1-ylethynyl-benzamide 
• 1413416-67-7 N-((3E)-3-(iodo(phenyl)methylene)isobenzofuran-1(3H)-ylidene)methanamine 
• 1439356-94-1 ethyl 6,7,8-trifluoro-2-(2-iodophenyl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 550-44-7 N-methylphthalimide 
• 1449378-46-4 3-(2,6-dimethylphenylimino)-2-methylisoindolin-1-one 
• 1449378-75-9 CF₃O₃S^(1-)*C₂₃H₃₂N₃OPd⁽¹⁺⁾ 
• 1449378-57-7 CF₃O₃S^(1-)*C₂₄H₃₂N₃O₃Pd⁽¹⁺⁾ 
• 1449378-59-9 CF₃O₃S^(1-)*C₂₅H₃₄N₃O₃Pd⁽¹⁺⁾ 
• 1449378-51-1 CF₃O₃S^(1-)*C₂₈H₃₄N₃OPd⁽¹⁺⁾ 
• 1449378-80-6 2,5-dimethyl-4-phenyl-2H-benzo[c]azepine-1,3-dione 
• 1449378-81-7 2-methyl-4,5-diphenyl-2H-benzo[c]-azepine-1,3-dione 

Relevant academic research and scientific papers

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides

A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.

Palladium-Catalyzed Domino Heck/C-H Activation/Decarboxylation: A Rapid Entry to Fused Isoquinolinediones and Isoquinolinones

A new palladium-catalyzed tandem cyclization of various alkene-tethered aryl iodides has been presented. In this protocol, o-bromobenzoic acids are employed as coupling parters to achieve the insertion of aromatic rings by the cleavage of C(sp2)-Br and decarboxylation, thus assembling various dibenzoisoquinolinediones and dibenzoisoquinolinones. In addition, a seven-membered ring can be constructed by the use of 8-bromo-1-naphthoic acid. Notably, this approach enables regioselective product formation and features broad substrate scope.

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.

Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones

Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).

Method for preparing axitinib and intermediates thereof

The invention discloses a method for preparing axitinib and intermediates thereof. A chemical name of the axitinib is N-methyl-2-[(3-(1E-2-(pyridine-2-yl)ethylene)-1H-indazole-6-yl)sulfur]benzamide, and a chemical formula of the axitinib is C22H18N4OS. The preparation process disclosed by the invention is simple in process, readily available in raw materials, economic, environmentally friendly, high in product yield and product purity, contributes to realizing industrialization, reduces the production cost and is suitable for mass production. The provided novel intermediates and the preparation method thereof have significance on the economic technology of the axitinib.

Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides

A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I2/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C=C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.

Ru(II)-Catalyzed C-H Activation: Amide-Directed 1,4-Addition of the Ortho C-H Bond to Maleimides

Maleimide has been used as a selective coupling partner to generate conjugate addition products exclusively. The typical Heck-type oxidative coupling that occurs when alkenes are used is avoided by choosing maleimide as an alkene, which cannot undergo β-hydride elimination due to the unavailability of a syn-periplanar β-hydrogen atom. The amide nitrogen, which is notorious for undergoing tandem reactions to generate spirocyclic or annulation products under cross-coupling conditions, remains innocent in this report. Along with the substrate scope, a robustness screen has been performed to analyze the performance of amide as a directing group in the presence of other directing groups and also to examine the tolerance of the reaction conditions for other frequently encountered functional groups.

Rhenium-catalyzed dehydrogenative olefination of C(sp3)-H bonds with hypervalent iodine(III) reagents

A dehydrogenative olefination of C(sp3)-H bonds is disclosed here, by merging rhenium catalysis with an alanine-derived hypervalent iodine(iii) reagent. Thus, cyclic and acyclic ethers, toluene derivatives, cycloalkanes, and nitriles are all successfully alkenylated in a regio- and stereoselective manner.