303975-71-5

Upstream product

• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 149377-19-5 4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 74-88-4 methyl iodide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 1510865-53-8 tert-butyl 4-(2-((4-methoxyphenyl)sulfonyl)hydrazono)piperidine-1-carboxylate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 1046478-89-0 tert-butyl 4-(p-tolylsulfonylhydrazono)-piperidine-1-carboxylate 
• 138647-51-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 66107-29-7 4-methoxyphenyl triflate 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 

Downstream Products

• 67259-62-5 4-(4-methoxyphenyl)piperidine 
• 6748-48-7 4-(4-methoxyphenyl)-piperidinehydrochloride 
• 1276045-16-9 1-[4-(4-methoxy-phenyl)-piperidin-1-yl]-ethanone 
• 1276045-15-8 cyclopropyl-[4-(4-methoxy-phenyl)-piperidin-1-yl]-methanone 
• 62614-84-0 4-(4-hydroxyphenyl)-1,2,3,6-tetrahydropiperidine 

Relevant academic research and scientific papers

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands

Cobalt(II) halides in combination with phenoxyimine (FI) ligands generated efficient precatalysts in situ for the C(sp2)-C(sp3) Suzuki-Miyaura cross-coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol %. Studies with alkyl halide electrophiles that function as radical clocks support the intermediacy of alkyl radicals during the course of the catalytic reaction. The improved performance of the FI-cobalt catalyst was correlated with decreased lifetimes of cage-escaped radicals as compared to those of diamine-type ligands. Studies of the phenoxyimine-cobalt coordination chemistry validate the L,X interaction leading to the discovery of an optimal, well-defined, air-stable mono-FI-cobalt(II) precatalyst structure.

Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in waterviasynergistic nickel and copper catalysis

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developedvianickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale.

Design, Synthesis, and Pharmacological Characterization of Heterobivalent Ligands for the Putative 5-HT2A/mGlu2Receptor Complex

We report the synthesis of the first series of heterobivalent ligands targeting the putative heteromeric 5-HT2A/mGlu2 receptor complex, based on the 5-HT2A antagonist MDL-100,907 and the mGlu2 ago-PAM JNJ-42491293. The functional properties of monovalent and heterobivalent ligands were characterized in 5-HT2A-, mGlu2/Gqo5-, 5-HT2A/mGlu2-, and 5-HT2A/mGlu2/Gqo5-expressing HEK293 cells using a Ca2+ imaging assay and a [3H]ketanserin binding assay. Pronounced functional crosstalk was observed between the two receptors in 5-HT2A/mGlu2 and 5-HT2A/mGlu2/Gqo5 cells. While the synthesized monovalent ligands retained the 5-HT2A antagonist and mGlu2 ago-PAM functionalities, the seven bivalent ligands inhibited 5-HT-induced responses in 5-HT2A/mGlu2 cells and both 5-HT- and Glu-induced responses in 5-HT2A/mGlu2/Gqo5 cells. However, no definitive correlation between the functional potency and spacer length of the ligands was observed, an observation substantiated by the binding affinities exhibited by the compounds in 5-HT2A, 5-HT2A/mGlu2, and 5-HT2A/mGlu2/Gqo5 cells. In conclusion, while functional crosstalk between 5-HT2A and mGlu2 was demonstrated, it remains unclear how these heterobivalent ligands interact with the putative receptor complex.

BET INHIBITORS FOR MODULATING DUX4 EXPRESSION IN FSHD

The present disclosure provides BET inhibitors of the formula: wherein the variables are defined herein, as well as pharmaceutical compositions thereof. The present disclosure also provides methods of treating a patient comprising administering a bromo- and extra-terminal (BET) domain inhibitor for the treatment of FSHD which modulates DUX4 expression. In some embodiments, the present methods comprise using one or more BET inhibitors as a therapeutic agent for the treatment of FSHD patients including patients who are being treated with one or more palliative treatments such as therapy and/or agents which lead to increased muscle mass.

Practical synthesis of pharmaceutically relevant molecules enriched in sp3 character

The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach has been successfully applied in formats amenable to parallel synthesis, in an asymmetric sense, and in the preparation of molecules with annotated biological activity.

Reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl and heteroaryl bromides

Reductive cross-coupling allows the direct C-C bond formation between two organic halides without the need for preformation of an organometallic reagent. A method has been developed for the reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl or heteroaryl bromides. The developed conditions use an air-stable Ni(II) source in the presence of a diamine ligand and a metal reductant to allow late-stage incorporation of saturated heterocyclic rings onto aryl halides in a functional-group tolerant manner.

Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids

The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2-sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.

Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperdin-3-yl- cyclopropane carboxamide derivatives as novel melatonin receptor ligands

Two series of 4-arylpiperidinyl amide and N-arylpiperdin-3-yl-cyclopropane carboxamide derivatives exhibiting diverse functionality at rat MT1 and MT2 receptors are reported. Compounds 11f and 18b (MT 1/MT2 agonist) have human microsomal intrinsic clearance comparable to ramelteon.

Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents

(Chemical Equation Presented) Mix in water, stir. That is all that is required in this new approach to sp3-sp2 cross-couplings between an alkyl iodide and an aryl bromide, both potentially bearing functionality. They react under cata

Direct synthesis of 4-arylpiperidines via palladium/copper(I)-cocatalyzed negishi coupling of a 4-piperidylzinc iodide with aromatic halides and triflates

A general procedure for the synthesis of 4-arylpiperidines via the coupling of 4-(N-BOC-piperidyl)zinc iodide with aryl halides and triflates is presented. The reaction requires cocatalysis with both Cl2Pd(dppf) and a copper(I) species. An impr