cas 59142-68-6, 2-Bromo-4-fluorobenzaldehyde

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Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation
In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.
Hu, Rong-Bin,Lam, Ying-Pong,Ng, Wing-Hin,Wong, Chun-Yuen,Yeung, Ying-Yeung
p. 3498 - 3506
(2021/04/07)

Synthesis and inhibitory studies of phosphonic acid analogues of homophenylalanine and phenylalanine towards alanyl aminopeptidases
A library of novel phosphonic acid analogues of homophenylalanine and phenylalanine, containing fluorine and bromine atoms in the phenyl ring, have been synthesized. Their inhibitory properties against two important alanine aminopeptidases, of human (hAPN, CD13) and porcine (pAPN) origin, were evaluated. Enzymatic studies and comparison with literature data indicated the higher inhibitory potential of the homophenylalanine over phenylalanine derivatives towards both enzymes. Their inhibition constants were in the submicromolar range for hAPN and the micromolar range for pAPN, with 1-amino-3-(3-fluorophenyl) propylphosphonic acid (compound 15c) being one of the best low-molecular inhibitors of both enzymes. To the best of our knowledge, P1 homophenylalanine analogues are the most active inhibitors of the APN among phosphonic and phosphinic derivatives described in the literature. Therefore, they constitute interesting building blocks for the further design of chemically more complex inhibitors. Based on molecular modeling simulations and SAR (structure-activity relationship) analysis, the optimal architecture of enzyme-inhibitor complexes for hAPN and pAPN were determined.
Wanat, Weronika,Talma, Micha?,Dziuk, B?a?ej,Kafarski, Pawe?
p. 1 - 22
(2020/09/18)

Preparation method of 2-bromine-4-fluorobenzaldehyde
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-bromine-4-fluorobenzaldehyde. The method comprises the following steps that (1)4-fluorobenzaldehyde is dissolved in an acid solution to be prepared into 0.1 to 100mol/L of 4-fluorobenzaldehyde acid solution; (2) the temperature of the solution is raised to 30 to 100 DEG C; bromination reagents are added while stirring is performed; stirring reaction is performed for 1 to 24h; (3) the bromination reagents are added again; stirring reaction is performed for 24 to 72h; (4) after the reaction is finished, reaction liquid is poured into ice water; (5) water phases are extracted by alkane solvents; organic phases are merged and are washed; pressure reduction concentration isperformed to remove organic solvents; 2-bromine-4-fluorobenzaldehyde crude products are obtained; the crude products are refined; the target product of 2-bromine-4-fluorobenzaldehyde is obtained. Theraw materials are cheap and can be easily obtained; the used bromination reagents are environment-friendly water treatment agents; the purification method of the target product is simple; the industrial production is facilitated.
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Paragraph 0027; 0028; 0034; 0035; 0036; 0037

(2019/06/11)

Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation
A palladium-catalyzed aminopalladation reaction followed by nucleophilic addition with aldehydes and dehydration is described. This direct and operationally simple procedure provides a rapid and reliable approach to a wide range of functionalized tetrahydroisoquinolines with high selectivity. Mechanistic studies disclosed that the nucleophilic addition, performed via a highly ordered transition-state, is the turnover-limiting step in which the inherent β-hydride elimination of the key Csp3?Pd species was controlled by the confined conformation and the nucleophilicity of the Csp3?Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.
Hu, Yue,Xie, Yinjun,Shen, Zhiqiang,Huang, Hanmin
supporting information
p. 2473 - 2477
(2017/02/23)

Fe(III)-catalyzed trityl benzyl ether formation and disproportionation cascade reactions to yield benzaldehydes
During investigating water-compatible Lewis acids catalyzed etherifications using alcohols as alkylating reagents directly, we developed Fe(III)-catalyzed trityl benzyl ether formations irradiated by microwave. Then an in situ trityl benzyl ether formation and disproportionation cascade reaction was achieved to yield the benzaldehyde products with good functional group tolerances under neat conditions at relative higher temperatures. The substituent effects of the substrates on the etherification and disproportionation were explored by changing the substitutions on benzyl alcohols and triarylmethanols using chemical kinetic plots methods and the mechanism of the transformation was studied by crossover experiments. The etherification and disproportionation cascade process could be conveniently scaled up in laboratory without losing much efficiency.
Wang, Xiaoyu,Du, Chuan,Shi, Hui,Pang, Yadong,Jin, Shengfei,Hou, Yuqian,Wang, Yanshi,Peng, Xiaoshi,Xiao, Jianyong,Liu, Yang,Liu, Yongxiang,Cheng, Maosheng
p. 6744 - 6748
(2015/08/24)

Copper/imidazolium/TEMPO-catalyzed aerobic oxidation of benzylic alcohols in water
Various imidazolium salts bearing hydrophilic groups were prepared that reacted with copper powder to afford water-soluble? copper complexes of N-heterocyclic carbenes. These copper complexes can catalyze the selective oxidation of benzyl alcohols to the corresponding aldehydes in water at room temperature without the need for a base. Georg Thieme Verlag Stuttgart . New York.
Chen, Congyan,Liu, Bo,Chen, Wanzhi
p. 3387 - 3391
(2014/01/06)

Identification of prostaglandin D2 receptor antagonists based on a tetrahydropyridoindole scaffold
A new series of indole-based antagonists of the PGD2 receptor subtype 1 (DP1 receptor) was identified and the progress of the structure-activity relationship study to the identification of potent and selective antagonists is presented. Selective DP1 antagonists with high potency and selectivity were prepared. Of particular interest is the DP1 antagonist 26 with a Ki value of 1 nM for the DP1 receptor and an IC50 value of 4.6 nM in a DP1 functional assay for the inhibition of the PGD2 induced cAMP production in platelet rich plasma (PRP).
Beaulieu, Christian,Guay, Daniel,Wang, Zhaoyin,Leblanc, Yves,Roy, Patrick,Dufresne, Claude,Zamboni, Robert,Berthelette, Carl,Day, Stephen,Tsou, Nancy,Denis, Danielle,Greig, Gillian,Mathieu, Marie-Claude,O'Neill, Gary
p. 2696 - 2700
(2008/12/21)

Prostaglandin EP4 antagonist
Disclosed herein are methods and compositions related to compound 1 or a pharmaceutically acceptable salt, or a prodrug thereof (all of which are referred to hereafter, collectively or individually, as “compound 1”), which is an antagonist of a prostaglandin EP4 receptor, or is a prostaglandin EP4 antagonist. Also disclosed is a method comprising administering a prostaglandin EP4 antagonist to a mammal suffering from, or at risk of developing, a disease or condition selected from the group consisting of cancer, immunological disorders, neurodegenerative disorders, ocular diseases, hepatic diseases, renal diseases, septicemia, fibromyalgia, dermatological disorders, and antipyrexia.
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(2008/06/13)

AMINO-HETEROCYCLES AS VR-1 ANTAGONISTS FOR TREATING PAIN
the present invention provides a compound of formula (I): wherein V represents NR5, O, S, SO or S(O)2; W and X each independently represent CH or N; Y represents N, CH or C-Ar2, with the proviso that at least one, but no more than two, of W, X and Y are N; Z represents CH or C-Ar2, with the proviso that when Y is N or CH then Z is C-Ar2, and with the further proviso that when Y is C-Ar2 then Z is CH; Ar1 represents a fused 9 or 10 membered heterobicyclic ring system containing one, two, three or four heteroatoms selected from nitrogen, oxygen and sulfur, wherein at least one of the rings in said ring system is aromatic; Ar2 represents an aromatic ring selected from phenyl, pyridyl, pyrimidinyl and pyridazinyl which is optionally fused and substituted; R1 represents halogen, hydroxy, oxo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, haloC1-6alkyl, hydroxyC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, hydroxyC1-6alkoxy, C3-7cycloalkyl, C3-7cycloalkoxy, C3-5cycloalkylC1-4alkyl, cyano, nitro, SR6, SOR6, SO2R6, COR6, NR3COR6, CONR3R4, NR3SO2R6, SO2NR3R4, -(CH2)mcarboxy, esterified -(CH2)mcarboxy or -(CH2)mNR3R4; R2 represents hydrogen, halogen, hydroxy, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy, haloC1-6alkoxy, unsubstituted phenyl or phenyl substituted with one or two groups selected from halogen, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy or haloC1-6alkoxy; R3 and R4 are each independently hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl or fluoroC1-6alkyl; or R3 and R4 and the nitrogen atom to which they are attached together form a heteroaliphatic ring of 4 to 7 ring atoms, optionally substituted by one or two groups selected from hydroxy or C1-4alkoxy, which ring may optionally contain as one of the said ring atoms an oxygen or a sulfur atom, S(O), S(O)2, or NR5; R5 represents hydrogen, C1-4alkyl, hydroxyC1-4alkyl or C1-4alkoxyC1-4alkyl; R6 represents hydrogen, C1-6alkyl, fluoroC1-6alkyl, C3-7cycloalkyl, unsubstituted phenyl, or phenyl substituted with one or two groups selected from halogen, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy or haloC1-6alkoxy; m is either zero or an integer from 1 to 4; n is either zero or an integer from 1 to 3; or a pharmaceutically acceptable salt, N-oxide or a prodrug thereof; a pharmaceutical composition comprising it; its use in methods of treatment; use of it for the manufacture of a medicament for treating VR-1 related conditions such as those in which pain and/or inflammation predominate; and methods of treatment using it.
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Page 27

(2010/02/07)

Prostaglandin D2 antagonist
Disclosed herein is compound 1 or a pharmaceutically acceptable salt, or a prodrug thereof. Compound 1 is useful for treating or preventing a variety of diseases or conditions. Results presented herein also demonstrate that Compound 1 is a prostaglandin D2 antagonist, and as such is useful in the treatment or prevention of prostaglandin D2 mediated conditions or diseases. A method comprising administering a prostaglandin D2 antagonist to a mammal suffering from a disease or condition selected from the group consisting of the gastrointestinal tract disorders or diseases, hyperalgesia, allodynia, abdominal cramping, glaucoma, ocular hypertension, and ocular hypotension is also disclosed herein. Pharmaceutical compositions and products comprising compound 1 are also disclosed.
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(2008/06/13)

Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists
The present invention provides novel compounds represented by the general formula I. wherein m, n, X, Y, Z, R, R1and R2are as defined in the specification or a pharmaceutically acceptable salt thereof. The novel compounds are PGF2αantagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.
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(2008/06/13)

Interphenylene 7-oxabicyclic [2.2.1] heptane oxazoles as prostaglandin F2a antagonists
The present invention provides novel compounds represented by the general formula I. wherein m is an integer of from 1 to 3; n is 0 or an integer of from 1 to 4; R is selected from the group consisting of CO2H, CO2R6, CH2OH, CH2O R6 ?and CONR3R4; R1and R2are independently selected from the group consisting of H, R6, C1-C6alkenyl, C1-C6alkynyl, C3-C7cycloalkyl, C4-C12alkylcycloalkyl, C6-C10aryl, C7-C12alkyl aryl radicals and heteroatom-substituted derivatives thereof, wherein one or more of the hydrogen or carbon atoms in said radicals is replaced with a halogen, nitrogen or sulfur-containing radical; R3and R4are selected from the group consisting of H and R6; and X is selected from the group consisting of R6, hydroxy, N(R6)2, CON(R6)2, SR6, sulfoxy, sulfone, halogen, COOR6, NO2, CN and OR6, wherein R6is C1-C6alkyl, and pharmaceutically acceptable salts thereof. The novel compounds are PGF2αantagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.
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(2008/06/13)

Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2alpha antagonists
The present invention provides novel compounds represented by the general wherein m, n, X, Y, Z, R, R1 and R2 are as defined in the specification or a pharmaceutically acceptable salt thereof. The novel compounds are PGF2α antagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.
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(2008/06/13)

Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists
The present invention provides novel compounds represented by the general formula I. wherein m is an integer of from 1 to 3; n is 0 or an integer of from 1 to 4; R is selected from the group consisting of CO2H, CO2R6, CH2OH, CH2O R6P(O)(OH)2, ?and CONR3R4; R1and R2are independently selected from the group consisting of H, R6, C1-C6alkenyl, C1-C6alkynyl, C3-C7cycloalkyl, C4-C12alkylcycloalkyl, C6-C10aryl, C7-C12alkyl aryl radicals and heteroatom-substituted derivatives thereof, wherein one or more of the hydrogen or carbon atoms in said radicals is replaced with a halogen, nitrogen or sulfur-containing radical; R3and R4are selected from the group consisting of H and R6; and X is selected from the group consisting of H, R6, hydroxy, N(R6)2, CON(R6)2, SR6, sulfoxy, sulfone, halogen, COOR6, NO2, CN and OR6, wherein R6is C1-C6alkyl; Y is O or S; Z is N or CH and pharmaceutically acceptable salts thereof. The novel compounds are PGF2αantagonists, useful in pharmaceutical compositions for treating PGF2α-mediated disease responses such as inflammatory reactions relating to rheumatoid arthritis and psoriasis, reproductive disorders, bronchoconstrictive disorders (asthma), excessive bone breakdown (osteoporosis), peptic ulcers, heart disease, platelet aggregation and thrombosis.
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(2008/06/13)

Fused pyridine derivatives
The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.
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Example 224

(2010/01/30)

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.
Bauer,Duffy,Hoffman,Klioze,Kosley Jr.,McFadden,Martin,Ong
p. 1315 - 1324
(2007/10/05)

Substituted 1,3-dihydrospiro(isobenzofuran)s
Novel substituted 1,3-dihydrospiro[isobenzofuran]s and methods of preparing the same are described. These compounds are useful as antidepressants, tranquilizers, analgetic agents and intermediates therefor.
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(2008/06/13)