1979-52-8

Upstream product

• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 1895-39-2 sodium chlorodifluoroacetate 
• 36029-90-0 p-Methyl-α-(chlordifluormethyl)-α-(trifluormethyl)-benzylchlorid 
• 431-49-2 2-bromo-1,1,3,3,3-pentafluoropropene 
• 624-31-7 4-tolyl iodide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 36029-81-9 p-Methyl-α-(chlordifluormethyl)-α-(trifluormethyl)-benzylalkohol 
• 108-88-3 toluene 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 

Downstream Products

• 36029-74-0 1-Trifluormethyl-1-p-tolyl-2,2-diphenylethylen 
• 35462-71-6 1-(1,1,1,3,3,3-hexafluoropropan-2-yl)-4-methylbenzene 
• 2396-26-1 1-methyl-4-(perfluoropropan-2-yl)benzene 

Relevant academic research and scientific papers

An I(I)/I(III) Catalysis Route to the Heptafluoroisopropyl Group: A Privileged Module in Contemporary Agrochemistry

The heptafluoroisopropyl group is emerging as a privileged chemotype in contemporary agrochemistry and features prominently in the current portfolio of leading insecticides. To reconcile the expansive potential of this module with the synthetic challenges

Structure-based Discovery of Phenyl (3-Phenylpyrrolidin-3-yl)sulfones as Selective, Orally Active RORγt Inverse Agonists

A new phenyl (3-phenylpyrrolidin-3-yl)sulfone series of RORγt inverse agonists was discovered utilizing the binding conformation of previously reported bicyclic sulfonamide 1. Through a combination of structure-based design and structure-activity relationship studies, a polar set of amides at N1-position of the pyrrolidine ring and perfluoroisopropyl group at para-position of the 3-phenyl group were identified as critical structural elements to achieve high selectivity against PXR, LXRα, and LXRβ. Further optimization led to the discovery of (1R,4r)-4-((R)-3-((4-fluorophenyl)sulfonyl)-3-(4-(perfluoropropan-2-yl)phenyl)pyrrolidine-1-carbonyl)cyclohexane-1-carboxylic acid (26), which displayed excellent selectivity, desirable liability and pharmacokinetic properties in vitro, and a good pharmacokinetic profile in mouse. Oral administration of 26 demonstrated dose-dependent inhibition of IL-17 production in a mouse IL-2/IL-23-induced pharmacodynamic model and biologic-like efficacy in an IL-23-induced mouse acanthosis model.

CARBOCYCLIC SULFONE RORγ MODULATORS

Described are RORγ modulators of the formula (I), or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein all substituents are defined herein. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

Background: 1,1-Difluoroalkenes cannot only be used as valuable precursors for organic synthesis, but also act as bioisosteres for enzyme inhibitors. Among various methods for their preparation, the carbonyl olefination with difluoromethylene phosphonium ylide represents one of the most straightforward methods. Results: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane (TMSCF3) in this reaction. Conclusion: Similar to many other Wittig-type gem-difluoroolefination reactions in the presence of PPh3, the reaction of TMSCF2Cl with aldehydes and activated ketones is effective.

Preparation of β,β-Difluoro-α-(trifluoromethyl)styrenes by Palladium-Catalyzed Coupling of Aryl Iodides with Pentafluoropropen-2-ylzinc Reagent

Substituted aromatic iodides are functionalized by pentafluoropropen-2-ylzinc, CF3C(ZnX)=CF2 (X = Br, I, or CF2=CCF3-), in the presence of Pd(PPh3)4 to give the corresponding arenes in good yields.This is particularly attractive for the preparation of title styrenes substituted with groups such as -NO2 or CO2R, which are incompatible with organomagnesium reagents.The best yields of the title styrenes with electron-donating substituents were obtained in DMF.For electron-withdrawing substituents, the best results were achieved in triglyme.A correlation was observed between Hammett ? constants and 19F NMR chemical shifts (R = 0.93-0.99, n = 8) and 2JF-F coupling constants (R = 0.94, n = 8).