14618-45-2 Usage
Description
3-(Trifluoroacetyl)indole is a heterocyclic trifluoromethyl ketone derived from the reaction of indole with trifluoroacetic anhydride. It is a versatile chemical compound with various applications in the field of organic synthesis and pharmaceutical chemistry.
Uses
Used in Pharmaceutical Chemistry:
3-(Trifluoroacetyl)indole is used as a reactant for the enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylation. This application is significant for the development of chiral drugs with improved efficacy and reduced side effects.
Used in Organic Synthesis:
1. 3-(Trifluoroacetyl)indole is used as a reactant for the preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives with indolecarboxylic acid. This reaction is crucial for the synthesis of complex molecular structures with potential applications in various industries.
2. It is also used as a reactant for the preparation of mast cell tryptase inhibitors, starting from indoles. Amidation serves as the key step in this process, which is essential for the development of novel therapeutic agents targeting mast cell-related diseases.
3. Additionally, 3-(Trifluoroacetyl)indole is used as a reactant for the formation of Michael adducts via the Baylis-Hillman reaction. This reaction is an important tool in organic synthesis, allowing for the creation of new carbon-carbon bonds and the synthesis of various organic compounds.
4. Furthermore, it is used as a reactant for the preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides. This reaction contributes to the synthesis of diverse indole-based compounds with potential applications in various fields.
Check Digit Verification of cas no
The CAS Registry Mumber 14618-45-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,1 and 8 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14618-45:
(7*1)+(6*4)+(5*6)+(4*1)+(3*8)+(2*4)+(1*5)=102
102 % 10 = 2
So 14618-45-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H6F3NO/c11-10(12,13)9(15)7-5-14-8-4-2-1-3-6(7)8/h1-5,14H
14618-45-2Relevant articles and documents
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Cipiani et al.
, p. 2595 (1976)
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Mackie et al.
, p. 437,442 (1977)
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Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation
Basak, Shubhajit,Paul, Tripti,Punniyamurthy, Tharmalingam
supporting information, p. 554 - 558 (2022/01/20)
Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.
Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays
Dang, Huong,Feichtinger, Konrad,Frazer, John,Grottick, Andrew J.,Kasem, Michelle,Le, Minh,Lehman, Juerg,Morgan, Michael E.,Ren, Albert,Sage, Carleton R.,Schrader, Thomas O.,Semple, Graeme,Unett, David J.,Whelan, Kevin T.,Wong, Amy,Zhu, Xiuwen
supporting information, (2020/01/22)
A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clinically studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.
