205187-05-9

Upstream product

• 372-20-3 3-fluorophenol 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 863870-75-1 O-2-bromo-3-fluorophenyl N,N-diethylcarbamate 
• 1244652-04-7 2-butyl-4-fluoro-1H-indole 
• 1244651-31-7 N-(3-fluoro-2-iodophenyl)-2-hydroxy-2-methylpropanamide 
• 1287792-06-6 4-fluoro-2-pentyl-3-(phenylthio)-1H-indole 
• 1287791-63-2 2-(3-fluoro-2-iodophenoxy)-2-methylpropanamide 
• 1287791-64-3 2-(2-bromo-3-fluorophenoxy)-2-methylpropanamide 
• 1287791-65-4 2-(2-chloro-3-fluorophenoxy)-2-methylpropanamide 
• 1287791-74-5 N-(2-bromo-3-fluorophenyl)-2-hydroxy-2-methylpropanamide 
• 1287791-75-6 N-(2-chloro-3-fluorophenyl)-2-hydroxy-2-methylpropanamide 
• 21397-08-0 2-chloro-3-fluoroaniline 
• 111721-75-6 2-bromo-3-fluoroaniline 
• 863870-89-7 4-fluoro-2-phenylbenzo[b]furan 

Relevant academic research and scientific papers

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

KINASE INHIBITOR

[Problem] To provide a novel PIM-3 inhibitor and a novel cancer therapeutic drug, in particular, a therapeutic drug for pancreatic cancer. [Solution] A PIM-3 kinase inhibitor comprising a compound represented by general formula (I) or a pharmacologically acceptable salt, hydrate or solvate thereof.

Palladium-catalysed ortho-arylation of carbamate-protected phenols

The carbamate (-O2CNR2) function is an excellent directing group for palladium-catalysed direct arylation reactions giving both protected or free mono- or di-substituted phenols, as well as an example of a dibenzopyranone, depending on coupling partners (aryl iodides or diaryliodonium salts) and conditions. The Royal Society of Chemistry 2009.

A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols

Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc

Directed ortho metalation reactions of aryl O-carbamates; a regiospecific synthesis of 2,2-disubstituted 2H-1-benzopyrans

A one-pot regiocontrolled synthesis of 2,2-disubstituted 2H-1-benzopyrans 5 from aryl O-carbamates 4 using the directed ortho metalation reaction is described and constitutes an advantageous complement to classical routes for this class of heterocycles.