59142-57-3

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 98-88-4 benzoyl chloride 
• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 59142-59-5 (2-Bromo-4-methoxy-phenyl)-phenyl-methanol 
• 74317-85-4 2-bromo-4-methoxybenzoic acid 

Downstream Products

• 611-94-9 4-Methoxybenzophenone 
• 15144-82-8 3-methoxy-fluoren-9-one 
• 74317-85-4 2-bromo-4-methoxybenzoic acid 

Relevant academic research and scientific papers

Palladium(II)-catalyzed Intermolecular Cascade Cyclization of Methylenecyclopropanes with Aromatic Alkynes: Construction of Spirocyclic Compounds Containing Indene and 1,2-Dihydronaphthalene Moieties

A palladium(II)-catalyzed intermolecular cascade cyclization of methylenecyclopropanes with aromatic alkynes is reported in this paper. The reaction involves a migratory insertion of alkyne, an intramolecular Heck-type reaction, and β-H elimination, providing a series of spirocyclic compounds containing indene and 1,2-dihydronaphthalene moieties in moderate to excellent yields upon heating.

Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes

The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

Synthesis and biological evaluation of negative allosteric modulators of the Kv11.1(hERG) channel

We synthesized and evaluated a series of compounds for their allosteric modulation at the Kv11.1 (hERG) channel. Most compounds were negative allosteric modulators of [3H]dofetilide binding to the channel, in particular 7f, 7h-j and 7p. Compounds 7f and 7p were the most potent negative allosteric modulators amongst all ligands, significantly increasing the dissociation rate of dofetilide in the radioligand kinetic binding assay, while remarkably reducing the affinities of dofetilide and astemizole in a competitive displacement assay. Additionally, both 7f and 7p displayed peculiar displacement characteristics with Hill coefficients significantly distinct from unity as shown by e.g., dofetilide, further indicative of their allosteric effects on dofetilide binding. Our findings in this investigation yielded several promising negative allosteric modulators for future functional and clinical research with respect to their antiarrhythmic propensities, either alone or in combination with known Kv11.1 blockers.

Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst

Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.

Synthesis of spiro[isobenzofuran 1(3H),4' piperidines] as potential central nervous system agents

Synthesis of 1' methyl 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] (7a, HP 365) and the demethyl analogue 9a (HP 505) was prompted by recognition of an aminoalkyl(aryl)isobenzofuran moiety common to the antidepressants talopram (Lu 3-010) and trans 10,11 dihydro 5,10 epoxy 5 [3 (methylamino)propyl] 5H dibenzo[a,d]cyclohepten 11 ol (MK-940). Convenient laboratory synthesis of 7a was provided by lithiation of 2 bromobenzhydryl methyl ether, followed by addition of 1 methyl 4 piperidone and acid catalyzed cyclization. N Dealkylation by standard methods afforded 9a. Synthesis of analogues was stimulated by discovery of marked inhibition of tetrabenazine induced ptosis for lead compounds 7a and 9a. Optimal antitetrabenazine activity is associated with the 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] moiety where nitrogen is basic. Modification of this moiety by introduction of large nitrogen substituents or a C-3 substituent > H significantly reduced antitetrabenazine activity. A series of analogue with aromatic substituents was investigated; however, few of these compounds were significantly more active than 7a and 9a. Compound 9a was selected for additional studies.