A5035442094- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Oxidative Organic Chemistry Reactions
- Synthesis and Catalytic Reactions
- Vanadium and Halogenation Chemistry
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Asymmetric Synthesis and Catalysis
- Chemical Synthesis and Reactions
- Cyclopropane Reaction Mechanisms
- Catalytic Cross-Coupling Reactions
- Synthetic Organic Chemistry Methods
- Advanced Synthetic Organic Chemistry
- Radical Photochemical Reactions
- Fluorine in Organic Chemistry
- Catalytic C–H Functionalization Methods
- Innovative Microfluidic and Catalytic Techniques Innovation
- Nanomaterials for catalytic reactions
- Computational Drug Discovery Methods
- Historical Medical Research and Treatments
- Carbohydrate Chemistry and Synthesis
- Machine Learning in Materials Science
- Inorganic Fluorides and Related Compounds
- Chemical Reaction Mechanisms
- Organometallic Complex Synthesis and Catalysis
Bristol-Myers Squibb (United States)
2008-2024
The Bristol-Myers Squibb Children's Hospital
2022
Bristol-Myers Squibb (Germany)
2010
IIT@MIT
2006
Massachusetts Institute of Technology
2006
Universidad de Oviedo
2001-2005
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at glance that was extracted from about 200 leading journals. To access Abstract, please click on HTML or PDF.
Ring-closing metathesis (RCM) has become indispensable in organic synthesis for both academic investigations and industrial applications. This review provides an overview of RCM reactions, focusing on the practical aspects that researchers environment may find interest. Key elements reaction design lessons learned from these applications are discussed to help those considering implementing reactions scale, particularly manufacturing active pharmaceutical ingredients (APIs). Advances...
Abstract The outstanding ability of dirhodium α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropanoate [Rh 2 (esp) ; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropanoate] to catalyze the cyclopropanation a wide range alkenes with malonate‐derived carbenoids under mild reaction conditions is reported in this communication. experimental protocol remarkably simple, uses readily accessible and stable dimethyl diazomalonate very low catalyst loading. More importantly, alkene employed as limiting reagent.
We describe the development and scale-up of a nickel-catalyzed reductive cross-electrophile coupling reaction between substituted 2-chloropyridine ethyl 3-chloropropanoate using manganese dust as terminal reductant. Several additives were screened for activation reductant in situ, chlorotriethylsilane (TESCl) was found to provide optimal conversion. A focused beam reflectance measurement (FBRM) probe utilized monitor particle attrition well during reaction. Modeling employed garner an...
The use of bis(pyridine)iodonium tetrafluoroborate (IPy(2)BF(4)) as an oxidizing agent towards different types alcohols is reported. observed reactivity involves reaction pathways, a function both the structures starting materials and experimental conditions. Interestingly, title iodine-containing compound capable tuneable with simple cycloalkanols, providing straight selective access either to omega-iodocarbonyl compounds or ketones, previously unreported chemoselective range oxidation...
You can also choose from alkanes! Either mono- or bifunctional iodo derivatives be prepared alkanes (see scheme) in an efficient and selective manner by using PhI(OAc)2, I2, alcohol.
We report research and development conducted to enable the safe implementation of a highly enantioselective palladium-catalyzed desymmetrization meso–bis-ester using trimethylsilylazide (TMSN3) as nucleophile. This work is used case example discuss practices when considering use azide reagents or intermediates, with focus on thermodynamic quantitative analysis hazards associated hydrazoic acid (HN3).
Abstract An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), a highly convenient oxidant such as hydrogen peroxide. Addition protic acid triggers faster process, role formally related that played by haloperoxidase enzymes naturally occurring transformations. The successful application these conditions multigram scale preparations over...
The process development and the kilogram-scale synthesis of linrodostat (BMS-986205, 1) are described. features several highly efficient telescoped processes use Evans auxiliary to install a methyl-bearing stereocenter. target was prepared in 12 steps with 7 isolations an overall yield 31%.
Herein we describe a series of synthetic efforts to prepare an advanced GPR40 agonist (compound 1), with focus on phase-appropriate processes that circumvented key reagents short supply in the original synthesis. The transformations refined for large-scale production were asymmetric aldol reaction, O-alkylation unstable intermediate, selective (Z)-olefination, and reduction Weinreb amide aldehyde. Additionally, new route stability issues core pyrrolidine fragment through de novo synthesis,...
Using water as the reaction medium, ketones can be transformed into α-iodoketones upon treatment with sodium iodide, hydrogen peroxide and an acid; interestingly, also obtained from secondary alcohols through a metal-free tandem oxidation–iodination approach.
Unactivated CH bonds react with iodine when exposed to trimethylsilyl azide in the presence of a hypervalent reagent or, alternatively, aqueous H2O2, acetic anhydride, and sodium (see scheme). Supporting information for this article (13C NMR spectra compounds 2 a–k) is available on WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501195_s.pdf or from author. Please note: The publisher not responsible content functionality any supporting supplied by authors. Any queries (other than...
Simply mix and switch on the light: This is all that required to obtain ω-functionalized aldehydes ketones from readily available cyclic alcohols IPy2BF4. The unusual oxidation process outlined in Equation (1). R1,R2=H, CH3; n=2, 3, 4, 10; Py=pyridine.
This communication highlights the use of chiral sulfinamides as nitrogen nucleophiles in intermolecular aza-Michael reactions. When are coupled to a chloroethyl group, corresponding novel annulating reagents can be used streamline stereoselective synthesis complex pyrrolidine-containing molecules. As result, it has enabled medicinal chemistry campaign for biologically active RORγt inverse agonists.
Abstract The concise synthesis of a pharmaceutical candidate is described. chiral core the molecule assembled using an aza‐benzoin condensation and dynamic kinetic resolution (DKR) as key reactions. This enables superb control regio‐, diastereo‐ enantioselectivity synthesis. Both biocatalysts transition metal catalysts are remarkably effective in asymmetric reduction step. Similar approaches could be considered other 1,2‐amino alcohols where traditional based on functionalization alkenes,...
A syn-selective synthesis of β-branched α-amino acids has been developed based on the alkylation glycine imine esters with secondary sulfonates. The potassium counterion for enolate, solvent, and leaving group electrophile were key levers to maximize diasteroselectivity alkylation. optimized conditions enabled a straightforward preparation number that can be challenging obtain.
The title compound, C10H10IN2+·BF4−, or IPy2BF4, is found to crystallize in the monoclinic crystal system. asymmetric unit contains two tetrafluoroborate anions, one independent IPy2 cation and half-cations; for latter I atoms lie on centres of symmetry. A slight deviation from planarity observed crystallographically cation.
Mono- oder difunktionelle Iodderivate lassen sich je nach Reaktionsbedingungen mithilfe des Reagenssystems PhI(OAc)2/I2 in Gegenwart eines Alkohols aus Alkanen erhalten (siehe Schema).
We report herein the development and scale up of an Ir-catalyzed N-alkylation reaction between a 4-bromopyridin-2-amine (1) (4-(5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-yl)bicyclo[2.2.2]octan-1-yl)methanol (2) proceeding via borrowing hydrogen process. The traditional approach alcohol oxidation followed by reductive amination posed challenges that are attributed to poor nucleophilicity 2-aminopyridine derivative resulting in lower isolated yields. Several catalysts bases were evaluated for...
We report research focused on the preparation of an advanced intermediate in synthesis a novel antiretroviral. This manuscript describes development efficient oxidation 6-azaindole derivative, bromination resulting N-oxide using PyBroP, removal protecting group, and isolation brominated azaindole product. The work reported herein has been successfully implemented multikilogram scale to fund clinical activities BMS-663068.
BMS-986251, a potent and efficacious RORγt inverse agonist, was synthesized starting from 6-iodotetralone using 13 chemical transformations with only eight isolated intermediates. The synthesis involved four-step telescoped diastereoselective aza-Michael reaction-annulation sequence followed by installation of the heptafluoro-iso-propyl side chain final amidation to furnish desired API.
The cyclohexane dicarboxylate unit of BMS-986251 (1), a potent and efficacious RORγt inverse agonist, was synthesized starting from Hagemann's ester in seven chemical transformations with five isolated intermediates. synthesis involved an enzymatic kinetic resolution, two-step telescoped enol tosylation followed by carboxylation using benign CO surrogate for the installation second carboxylate functionality, Crabtree catalyst-mediated diastereoselective olefin hydrogenation. This process...
Nichtaktivierte C-H-Bindungen reagieren mit Iod in Gegenwart von Trimethylsilylazid und hypervalenten Iodreagentien oder, alternativ, wässrigem H2O2, Essigsäureanhydrid Natriumazid (siehe Schema). Supporting information for this article (13C NMR spectra of compounds 2 a–k) is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2005/z501195_s.pdf or from author. Please note: The publisher not responsible content functionality any supporting supplied by authors. Any queries...
BMS-813160 is a pharmaceutical entity currently in development at Bristol Myers Squibb. Its defining structural feature unique chiral all cis triamino cyclohexane core. Medicinal and process chemistry groups BMS have previously published synthesis strategies for chemotypes similar to the target molecule, but streamlined approach amenable longer-term supply was necessary. A new synthetic route conceptualized, experimentally investigated, determined meet criteria efficiency that addressed key...