- A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols
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2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).
- Vazquez, Enrique,Davies, Ian W.,Payack, Joseph F.
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Read Online
- Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction
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The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.
- Hua, Xiye,Masson-Makdissi, Jeanne,Sullivan, Ryan J.,Newman, Stephen G.
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supporting information
p. 5312 - 5315
(2016/11/02)
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- 1,3,5-TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF
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The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH2 or a group -NHSO2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use
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Page/Page column 17
(2013/07/05)
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- A trans diacyloxylation of indoles
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A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions. The Royal Society of Chemistry 2012.
- Liu, Qiang,Zhao, Qing Yong,Liu, Jie,Wu, Pan,Yi, Hong,Lei, Aiwen
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supporting information; experimental part
p. 3239 - 3241
(2012/04/10)
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- Palladium catalyzed tandem alkenyl- and aryl-C-N bond formation: A cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles
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A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile.
- Henderson, Luke C.,Lindon, Matthew J.,Willis, Michael C.
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experimental part
p. 6632 - 6638
(2010/10/03)
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- NOVEL P2X7R ANTAGONISTS AND THEIR USE
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The present application is directed to novel P2X7R antagonists that are N-indol-3-yl-acetamide and N-azaindol-3-yl-acetamide compounds, pharmaceutical compositions comprising the same and their use for the prophylactic or therapeutic treatment of diseases
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Page/Page column 7-8
(2010/11/03)
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- 2-PHENYL-INDOLES AS PROSTAGLANDIN D2 RECEPTOR ANTAGONISTS
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The present invention is directed to 2-phenyl-indole compounds (A), their preparation, pharmaceutical compositions containing these compounds, and their pharmaceutical use in treating a patient suffering from a PGD2-mediated disorder including, but not li
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Page/Page column 41; 43
(2008/06/13)
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- Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines
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Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).
- Clark,Muchowski,Fisher,Flippin,Repke,Souchet
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p. 871 - 878
(2007/10/02)
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