70001-45-5Relevant academic research and scientific papers
Synthesis method of lapatinib intermediate
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Paragraph 0028; 0029, (2021/05/01)
The invention discloses a synthesis method of a lapatinib intermediate, and belongs to the technical field of organic synthesis. The method comprises the following steps: performing carboxyl protection on p-fluorobenzoic acid serving as a raw material and adding acetyl at an ortho-position to obtain a compound IV, performing chiral reduction on the compound IV to obtain a compound V with S configuration, performing Mitsunobu reaction on the compound V and 3-hydroxy-2-nitropyridine to obtain a compound VI with R configuration, performing reaction on the compound VI and hydrochloric acid methanol to obtain a compound VII, and performing recrystallization to obtain the compound VII. and finally, performing nitro-reduction to obtain products. The method has the advantages that the initial raw materials are cheap and easy to obtain (the price of p-fluorobenzoic acid is far lower than that of the raw materials in the prior art), the stereoselectivity is good, chiral resolution is not needed, the total yield is high (the existing yield is about 20%, and the patent is larger than 40%), and a feasible scheme is provided for lapatinib process research.
σ-Bond Hydroboration of Cyclopropanes
Arifin,Itami, Kenichiro,Kato, Hiroki,Kobayashi, Chisa,Kondo, Hiroki,Matsushita, Kaoru,Miyamura, Shin,Yamaguchi, Junichiro,Yokogawa, Daisuke
supporting information, p. 11306 - 11313 (2020/07/13)
Hydroboration of alkenes is a classical reaction in organic synthesis in which alkenes react with boranes to give alkylboranes with subsequent oxidation resulting in alcohols. The double bond (π-bond) of alkenes can be readily reacted with boranes owing to its high reactivity. However, the single bond (σ-bond) of alkanes has never been reacted. To pursue the development of σ-bond cleavage, we selected cyclopropanes as model substrates since they present a relatively weak σ-bond. Herein, we describe an iridium-catalyzed hydroboration of cyclopropanes, resulting in β-methyl alkylboronates. These unusually branched boronates can be derivatized by oxidation or cross-coupling chemistry, accessing "designer"products that are desired by practitioners of natural product synthesis and medicinal chemistry. Furthermore, mechanistic investigations and theoretical studies revealed the enabling role of the catalyst.
Chemoselective synthesis of naphthylamides and isoquinolinones via rhodium-catalyzed oxidative dehydrogenative annulation of benzamides with alkynes
Shi, Zhuangzhi,Tang, Conghui,Jiao, Ning
supporting information, p. 2695 - 2700 (2013/01/15)
A rhodiumACHTUNGTRENUNG(III)-catalyzed direct dehydrogenative annulation of benzamides with alkynes through chelating-assisted C-H activation has been developed. Naphthylamide and isoquinolinone derivatives can be chemoselectively obtained by this protoco
Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
Przychodzen, Witold
, p. 676 - 684 (2007/10/03)
To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes kT2 and kR2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.
