134368-62-0Relevant academic research and scientific papers
An Improved Synthesis of the Free Base and Diglycolate Salt of CEP-33779; A Janus Kinase 2 Inhibitor
Levy, Daniel V.,Sclafani, Joseph A.,Bakale, Roger P.
, p. 2085 - 2091 (2016/12/24)
CEP-33779 is a triazole that has been reported to show highly selective inhibition of Janus kinase 2 (JAK2). An efficient process to form CEP-33779 will be presented that uses multiple palladium couplings to provide the drug substance in a convergent mann
Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines
Qian, Xin,Yu, Zailu,Auffrant, Audrey,Gosmini, Corinne
supporting information, p. 6225 - 6229 (2013/07/05)
Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright
Replacing conventional carbon nucleophiles with electrophiles: Nickel-catalyzed reductive alkylation of aryl bromides and chlorides
Everson, Daniel A.,Jones, Brittany A.,Weix, Daniel J.
supporting information; experimental part, p. 6146 - 6159 (2012/05/07)
A general method is presented for the synthesis of alkylated arenes by the chemoselective combination of two electrophilic carbons. Under the optimized conditions, a variety of aryl and vinyl bromides are reductively coupled with alkyl bromides in high yields. Under similar conditions, activated aryl chlorides can also be coupled with bromoalkanes. The protocols are highly functional-group tolerant (-OH, -NHTs, -OAc, -OTs, -OTf, -COMe, -NHBoc, -NHCbz, -CN, -SO2Me), and the reactions are assembled on the benchtop with no special precautions to exclude air or moisture. The reaction displays different chemoselectivity than conventional cross-coupling reactions, such as the Suzuki-Miyaura, Stille, and Hiyama-Denmark reactions. Substrates bearing both an electrophilic and nucleophilic carbon result in selective coupling at the electrophilic carbon (R-X) and no reaction at the nucleophilic carbon (R-[M]) for organoboron (-Bpin), organotin (-SnMe3), and organosilicon (-SiMe2OH) containing organic halides (X-R-[M]). A Hammett study showed a linear correlation of σ and σ(-) parameters with the relative rate of reaction of substituted aryl bromides with bromoalkanes. The small ρ values for these correlations (1.2-1.7) indicate that oxidative addition of the bromoarene is not the turnover-frequency determining step. The rate of reaction has a positive dependence on the concentration of alkyl bromide and catalyst, no dependence upon the amount of zinc (reducing agent), and an inverse dependence upon aryl halide concentration. These results and studies with an organic reductant (TDAE) argue against the intermediacy of organozinc reagents.
New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust
Fillon, Hyacinthe,Gosmini, Corinne,Perichon, Jacques
, p. 3867 - 3870 (2007/10/03)
A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.
