379-95-3Relevant academic research and scientific papers
PROCESSES FOR MAKING SERD TRICYCLIC COMPOUNDS HAVING A SUBSTITUTED PHENYL OR PYRIDINYL MOIETY
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Paragraph 0330-0331, (2022/01/12)
Provided herein are processes for the preparation of compounds useful in the treatment of cancer.
Efficient Manufacturing Process for the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) via a Crystallization-Driven Diastereoselective Pictet-Spengler Condensation
Chung, Cheol K.,Clagg, Kyle,Dalziel, Michael E.,Fettes, Alec,Finet, Laure,Gosselin, Francis,Jenny, Christian,Kammerer, Michael,Lim, Ngiap-Kie,Mack, Kyle A.,McClory, Andrew,Wuitschik, Georg,Xu, Jie,Zhang, Haiming,Angelaud, Rémy
, (2021/11/24)
GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545·tartrate.
Microwave-assisted rapid electrophilic fluorination of 1,3-dicarbonyl derivatives with Selectfluor
Xiao, Ji-Chang,Shreeve, Jean'ne M.
, p. 475 - 478 (2007/10/03)
A microwave-assisted fluorination method for 1,3-dicarbonyl compounds using Selectfluor has been developed. 2-Monofluorinated products can be obtained in high yield in neutral reaction conditions with addition of 1 eq. of Selectfluor. Treatment of 1,3-dicarbonyls with 3 eq. of Selectfluor in the presence of tetrabutylammonium hydroxide (TBAH) as the base results in the formation of 2,2-difluorinated derivatives only.
Perfluoroepoxycarboxylates. Preparation and some properties
Zapevalov,Filyakova,Kodess
, p. 1113 - 1116 (2007/10/03)
Perfluoroepoxycarboxylates were obtained by oxidation with molecular oxygen of esters of unsaturated perfluoroepoxycarboxylic acids CF2=CF(CF2)nCO2CH3 under UV irradiation. The isomeric transformations and thermal stability of the methyl pentafluoro-3,4-epoxybutanate were studied. In the reaction of the above compound with Et3N was obtained methyl tetrafluoro-3-fluoroformylpropanate, and with SbF5 on graphite arised methyl pentafluoroacetate.
Preparation of difluoromalonyl fluoride
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, (2008/06/13)
Carboxylic ester and acyl fluoride groups are interchanged in the presence of a metal fluoride catalyst or a metal fluoride/strong sulfonic acid catalyst combination to produce fluorinated mono- and diacyl fluorides.
