18113-13-8Relevant academic research and scientific papers
Efficient 11C-carbonylation of isolated aryl palladium complexes for PET: Application to challenging radiopharmaceutical synthesis
Andersen, Thomas L.,Friis, Stig D.,Audrain, Hlne,Nordeman, Patrik,Antoni, Gunnar,Skrydstrup, Troels
supporting information, p. 1548 - 1555 (2015/03/05)
We describe the successful implementation of palladium-aryl oxidative addition complexes as stoichiometric reagents in carbonylation reactions with 11CO to produce structurally challenging, pharmaceutically relevant compounds. This method enables the first 11C-carbonyl labeling of an approved PET tracer, [11C]raclopride, for the dopamine D2/D3 receptor by carbonylation with excellent radiochemical purity and yield. Two other molecules, [11C]olaparib and [11C]JNJ 31020028, were efficiently labeled in this manner. The technique distinguishes itself from existing methods by the markedly improved purity profiles of the tracer molecules produced and provides access to complex structures in synthetically useful yields, hereby offering a viable alternative to other 11C-labeling strategies.
THE REACTIONS OF UNACTIVATED ARYL HALIDES WITH SODIUM METHOXIDE IN HMPA; SYNTHESIS OF PHENOLS, ANISOLES, AND METHOXYPHENOLS
Testaferri, L.,Tiecco, M.,Tingoli, M.,Chianelli, D.,Montanucci, M.
, p. 193 - 198 (2007/10/02)
Sodium methoxide reacts with dichlorobenzenes in HMPA to give the chloroanisoles as a result of a SNAr process.Excess MeONa then effects the demethylation of the ethers to give the chlorophenols via an SN2 reaction.With tri- and tetrachlorobenzenes the initially formed chloroanisoles can be dealkylated to chlorophenols or can suffer further substitution to give the chlorodimethoxybenzenes; these react with excess MeONa to give the chloromethoxyphenols.The results obtained with the various isomers of the di-, tri-, and tetrachlorobenzenes are presented and discussed on the basis of the electronic effects of the substituents.
