69038-73-9Relevant articles and documents
Total Synthesis of Entrectinib with Key Photo-Redox Mediated Cross-Coupling in Flow
Cordell, Morgan J.,Adams, Matt R.,Vincent-Rocan, Jean-Fran?ois,Riley, John G.
supporting information, (2021/12/30)
By using photo-redox catalysis in flow the newly marketed drug entrectinib (referred to by the brand name Rozlytrek) was synthesized in 6 linear steps from readily available building blocks under mild conditions. Evaluation of multiple intermediates for their use in the critical C?N amination step in flow led to the finding that more electron deficient aryl-halides achieve higher conversion to the desired product. Data supports that more electron rich aryl-halides undergo a significant amount of hydro-dehalogenation compared to the productive C?N bond formation. Through evaluating various entry points into the synthesis of entrectinib, shorter routes were identified albeit in low yields. The modularity of this route will allow chemists to rapidly synthesize a diverse library of compounds through this route. Via different synthetic intermediates, a scale-up route was discovered for the synthesis of entrectinib using photo-redox in flow in less steps than previously reported, highlighting the utility of flow chemistry in the pharmaceutical industry.
The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride
Greenberg, Jacob A.,Sammakia, Tarek
, p. 3245 - 3251 (2017/03/23)
The reaction of tert-butyl esters with SOCl2 at room temperature provides acid chlorides in unpurified yields of 89% or greater. Benzyl, methyl, ethyl, and isopropyl esters are essentially unreactive under these conditions, allowing for the selective conversion of tert-butyl esters to acid chlorides in the presence of other esters.
A mesoporous organosilica grafted Pd catalyst (MOG-Pd) for efficient base free and phosphine free synthesis of tertiary butyl esters via tertiary-butoxycarbonylation of boronic acid derivatives without using carbon monoxide
Ghosh, Kajari,Molla, Rostam Ali,Iqubal, Md. Asif,Islam
, p. 3540 - 3551 (2015/06/25)
A mesoporous organosilica grafted palladium(ii) catalyst was synthesized and characterized using various spectroscopic techniques. Its catalytic activity was evaluated for the synthesis of tertiary butyl esters via tert-butoxycarbonylation of boronic acid
