280752-68-3Relevant academic research and scientific papers
Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound
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Paragraph 0087-0092, (2021/04/03)
The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.
KRAS G12D INHIBITORS
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Paragraph 01516, (2021/03/05)
The present invention relates to compounds that inhibit KRas G12D. In particular, the present invention relates to compounds that inhibit the activity of KRas G12D, pharmaceutical compositions comprising the compounds and methods of use therefor.
Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
Huang, Mao-Gui,Shi, Shuai,Li, Ming,Liu, Yue-Jin,Liu, Yue-Jin
supporting information, p. 7094 - 7099 (2021/09/14)
A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.
Ascorbic Acid as an Aryl Radical Inducer in the Gold-Mediated Arylation of Indoles with Aryldiazonium Chlorides
Medina-Mercado, Ignacio,Asomoza-Solís, Eric Omar,Martínez-González, Eduardo,Ugalde-Saldívar, Victor Manuel,Ledesma-Olvera, Lydia Gabriela,Barquera-Lozada, José Enrique,Gómez-Vidales, Virginia,Barroso-Flores, Joaquín,Frontana-Uribe, Bernardo A.,Porcel, Susana
supporting information, p. 634 - 642 (2019/12/11)
In recent years interest in the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI. The aryl–AuIII species generated in this way, has been used to prepare 3-arylindoles in a one-pot protocol starting from anilines and para-, meta-, and ortho- substituted aryldiazonium chlorides. The mechanism underlying the oxidative addition has been examined in detail based on EPR analyses, cyclic voltammetry, and DFT calculations. Interestingly, we have found that in this protocol, the chloride atom induces the AuII/AuIII oxidation step.
Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides
Zhu, Ming-Hui,Yu, Cheng-Long,Feng, Ya-Lan,Usman, Muhammad,Zhong, Dayou,Wang, Xin,Nesnas, Nasri,Liu, Wen-Bo
supporting information, p. 7073 - 7077 (2019/09/30)
An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The application of this method is demonstrated by the introduction of isotope-labeled (CD3 and 13CH3) groups using the readily accessible labeled alcohols and the synthesis of pharmaceuticals.
PHENYL mTORC INHIBITORS AND USES THEREOF
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Paragraph 00394, (2018/05/27)
The present invention provides compounds, compositions thereof, and methods of using the same.
Indole-3-carbonitriles as DYRK1A inhibitors by fragment-based drug design
Meine, Rosanna,Becker, Walter,Falke, Hannes,Preu, Lutz,Loa?c, Nadège,Meijer, Laurent,Kunick, Conrad
, (2018/02/07)
Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer's disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3, 2-c]quinoline-6-carboxy
Thioether-Directed Selective C4 C-H Alkenylation of Indoles under Rhodium Catalysis
Kona, Chandrababu Naidu,Nishii, Yuji,Miura, Masahiro
supporting information, p. 4898 - 4901 (2018/08/24)
A thioether-directed Rh(III)-catalyzed C4 selective C-H alkenylation of indoles via the formation of 5-membered metallacycle intermediates is reported. This protocol allows a wide functional group compatibility and broad substrate scope. The directing group can be readily removed or transformed into other functional groups after the C-H functionalization event. The catalytic method is also applicable to related heterocyclic systems involving benzo[b]thiophene and benzo[b]furan scaffolds.
Copper-mediated trifluoroacetylation of indoles with ethyl trifluoropyruvate
Yan, Guobing,Cao, Xihan,Zheng, Wanbin,Ke, Qiumin,Zhang, Jieyu,Huang, Dayun
supporting information, p. 5904 - 5907 (2017/07/25)
Direct trifluoroacetylation of indoles with ethyl trifluoropyruvate as a trifluoroacetylating reagent has been developed. This novel protocol provides an attractive route for the preparation of 3-trifluoroacetylindole derivatives, due to its operational simplicity and practicability as well as mild reaction conditions.
Synthesis of phenanthridine skeletal Amaryllidaceae alkaloids
Fan-Chiang, Tai-Ting,Wang, Hung-Kai,Hsieh, Jen-Chieh
, p. 5640 - 5645 (2016/08/17)
Strategies for the synthesis of Amaryllidaceae alkaloids, including crinasiadine, trisphaeridine, bicolorine, N-methylcrinasiadine, 5,6-dihydrobicolorine, galanthindole, lycosinine A and lycosinine B were reported. Investigation of optionally synthetic routes to approach bicolorine, 5,6-dihydrobicolorine, trisphaeridine and N-methylcrinasiadine were demonstrated as well. In addition, three structurally related alkaloids galanthindole, lycosinine A and lycosinine B were concisely prepared by using Suzuki coupling reaction as the key step.
