63375-81-5

Usage

InChI:InChI=1/C10H14BrNO2/c1-13-9-5-7(3-4-12)8(11)6-10(9)14-2/h5-6H,3-4,12H2,1-2H3

Upstream product

• 51655-39-1 2-bromo-4,5-dimethoxyphenylacetonitrile 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 635-85-8 homoveratrylamine hydrochloride 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 90841-59-1 2-(2-bromo-4,5-dimethoxyphenyl)acetaldehyde 
• 289507-36-4 2-(2-bromo-4,5-dimethoxyphenyl)ethyl alcohol 
• 69327-12-4 1-bromo-2-(2-bromoethyl)-4,5-dimethoxybenzene 
• 6275-29-2 N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 74064-26-9 N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]acetamide 
• 67191-53-1 N-(3,4-Dimethoxyphenethyl)propionamide 
• 106469-78-7 tert-butyl (2-bromo-4,5-dimethoxyphenethyl)carbamate 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 

Downstream Products

• 134745-78-1 [2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-(7-methoxy-benzo[1,3]dioxol-4-ylmethyl)-amine 
• 75767-96-3 N-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin 
• 128741-53-7 [2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-[1-(3,4-dimethoxy-phenyl)-meth-(E)-ylidene]-amine 
• 74421-96-8 N-benzyl-2-bromo-4,5-dimethoxyphenethylamine 
• 162330-92-9 N-<β-(2-bromo-4,5-dimethoxyphenyl)ethyl>-3-amino-1-indanone 
• 190511-17-2 N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-2,3-didehydro-3-ethyl-6-heptyl-4-oxopiperidine 
• 211620-06-3 1-[2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-5-ethyl-2-(4-nitro-phenyl)-2,3-dihydro-1H-pyridin-4-one 
• 190510-99-7 1-(2-bromo-4,5-dimethoxyphenethyl)-2-phenyl-2,3-dihydropyridin-4(1H)-one 
• 190511-13-8 N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-2,3-didehydro-3-ethyl-4-oxo-6-phenylpiperidine 
• 190511-00-3 1-(2-bromo-4,5-dimethoxyphenethyl)-2-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-one 
• 190511-14-9 1-[2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-5-ethyl-2-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one 
• 190511-03-6 N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-2,3-didehydro-4-oxo-6-propylpiperidine 

Relevant academic research and scientific papers

L-DOPA Dioxygenase Activity on 6-Substituted Dopamine Analogues

Dioxygenase enzymes are essential protein catalysts for the breakdown of catecholic rings, structural components of plant woody tissue. This powerful chemistry is used in nature to make antibiotics and other bioactive materials or degrade plant material, but we have a limited understanding of the breadth and depth of substrate space for these potent catalysts. Here we report steady-state and pre-steady-state kinetic analysis of dopamine derivatives substituted at the 6-position as substrates of L-DOPA dioxygenase, and an analysis of that activity as a function of the electron-withdrawing nature of the substituent. Steady-state and pre-steady-state kinetic data demonstrate the dopamines are impaired in binding and catalysis with respect to the cosubstrate molecular oxygen, which likely afforded spectroscopic observation of an early reaction intermediate, the semiquinone of dopamine. The reaction pathway of dopamine in the pre-steady state is consistent with a nonproductive mode of binding of oxygen at the active site. Despite these limitations, L-DOPA dioxygenase is capable of binding all of the dopamine derivatives and catalyzing multiple turnovers of ring cleavage for dopamine, 6-bromodopamine, 6-carboxydopamine, and 6-cyanodopamine. 6-Nitrodopamine was a single-turnover substrate. The variety of substrates accepted by the enzyme is consistent with an interplay of factors, including the capacity of the active site to bind large, negatively charged groups at the 6-position and the overall oxidizability of each catecholamine, and is indicative of the utility of extradiol cleavage in semisynthetic and bioremediation applications.

Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position

Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σmconstant, confirming the electronic properties of substituents.

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.

FSH RECEPTOR ANTAGONISTS

The invention relates to FSH receptor antagonist according to general formula (I) or a pharmaceutically acceptable salt thereof and to a pharmaceutical composition containing the same. The compounds can be used for the treatment and prevention of endometriosis, for the treatment and prevention of pre-menopausal and peri-menopausal hormone-dependent breast cancer, for contraception, and for the treatment of uterine fibroids and other menstrual-related disorders

Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams

Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright

Improved arene fluorination methodology for I(III) salts

(Equation Presented). The use of low polarity aromatic solvents (benzene or toluene) and/or the removal of inorganic salts results in dramatically improved yields of fluorinated arenes from diaryliodonium salts. This methodology is shown to "scale down" to the conditions used typically for radiotracer synthesis.

FLUORINATION OF AROMATIC RING SYSTEMS

This disclosure relates to reagents and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18F labeled radiotracers. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

Regioselective, photochemical bromination of aromatic compounds using N-bromosuccinimide

Regioselective nuclear bromination of aromatic compounds is investigated with N-bromosuccinimide as the brominating agent under UV irradiation to afford the corresponding brominated compounds. The reaction proceeds at ambient temperature (30 ± 2 °C) without any catalyst. In most of the reactions, regioselectively mono-brominated products are obtained in good to high yields. The conversion and selectivity for bromination depend on the nature of the substituent on the aromatic ring.

Generation of a small library of highly electron-rich 2-(hetero)aryl- substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue

The Suzuki-Miyaura reaction is presented as a versatile procedure for the synthesis of a small library of highly electronrich 2-[4,5-dimethoxy-2-(hetero) arylphenyl]ethylamines. Microwave-irradiation accelerates the reaction tremendously and furnishes superior yields. The difficult oxidative addition of the catalyst to a highly electron-rich and ortho-substituted system could be performed easily, and the proto-deboronation during cross-coupling reactions involving the highly electron-withdrawing (2-formylphenyl)boronic acid could be minimized. Enhanced yields and complete compatibility with aqueous conditions were found. This strategy was developed en route towards the synthesis of an apogalanthamine analogue. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Photochemically induced cyclization of N-[2-(o-styryl)phenylethyl]acetamides and 5-styryl-1-methyl-1,2,3,4-tetrahydroisoquinolines: New total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines

Two new total syntheses of 1-methyl-1,2,3,4-dihydronaphtho[1,2-f]isoquinolines are based on photochemically induced cyclization of N-{2-[(E)-2-phenyl-1-etheynyl]phenylethyl]}acetamides or 1-methyl-5-[(E)-2-phenyl-1-ethenyl]-1,2,3,4-tetrahydroisoquinolines.