398-21-0Relevant academic research and scientific papers
Preparation methods of aprepitant impurity
-
Paragraph 0144-0145, (2020/07/13)
The invention discloses preparation methods of an aprepitant impurity, which comprise isomer impurity synthesis method of six aprepitant key intermediates (2R, 3S)-2-[(1R)-1-[3, 5-bis (trifluoromethyl)-phenyl] ethoxy]-3-(4-fluorophenyl) morpholine, respectively, synthesis of four diastereomer impurities, synthesis of one enantiomer impurity and synthesis of one by-product impurity. The methods have the beneficial effects that the five synthesis methods are simple and feasible, the raw materials are easy to obtain, the conditions are mild, the cost is low, the production is facilitated, and meanwhile, the isomer impurities of the synthesized aprepitant key intermediate provide a new intermediate raw material for the preparation of aprepitant.
Visible-Light-Promoted, Catalyst-Free Gomberg-Bachmann Reaction: Synthesis of Biaryls
Lee, Juyoung,Hong, Boseok,Lee, Anna
, p. 9297 - 9306 (2019/08/12)
Biaryls were synthesized via a novel visible-light-promoted Gomberg-Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor-acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.
New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer
Witzel, Sina,Sekine, Kohei,Rudolph, Matthias,Hashmi, A. Stephen K.
, p. 13802 - 13804 (2018/12/14)
The scope of photosensitizer-free visible light-driven gold-catalyzed cross-coupling was evaluated by a wide variety of organoboron and organosilicon species using four equivalents of aryldiazonium salts and (4-CF3-C6H4)3PAuCl in MeOH. In addition, a C(sp or sp2)-C(sp2) cross-coupling of organotrimethylsilanes and aryldiazonium salts was investigated. The reactions can be conducted under very mild reaction conditions, with a reduced amount of aryldiazonium salt (1.2 equiv.) by using a catalytic amount of Ph3PAuNTf2 in MeCN under irradiation with blue LEDs at room temperature.
Synthesis, characterization, and nonlinear optical (NLO) properties of truxene-cored diphenylamine derivatives
Li, Fusheng,Zhao, Baodong,Chen, Yu,Zhang, Yufei,Wang, Tao,Xue, Song
, p. 20 - 26 (2017/05/29)
Three star-shaped compounds based on a truxene core (FS11, FS12 and FS13) were prepared. The truxene core is incorporating with asymmetric diphenylamines, including one phenyl of diphenylamine substituted by methoxy group and the other phenyl substituted by tolyl, fluorophenyl and phenylethynyl for FS11, FS12 and FS13, respectively. Their one-photon, two-photon absorption, geometric structures, electrochemical behavior and thermal properties were investigated. The absorption maxima of charge transfer band for FS11, FS12 and FS13 are 375?nm, 373?nm and 383?nm, and the corresponding molar extinction coefficients of FS11, FS12 and FS13 is 79,950?M??1?cm??1, 67,220?M??1?cm??1 and 108,780?M??1?cm??1. The “pull-push” structure promotes charge transfer between asymmetric diphenylamine branches and the truxene core. Their two-photon absorbtion property is measured by two-photon induced fluorescence. The maximum two-photon cross-sections values of FS11, FS12 and FS13 are excited at 750?nm, which are 260 GM, 204GM and 367 GM, respectively.
C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents
Ding, Yuyang,Mao, Liufeng,Xu, Dengfeng,Xie, Hui,Yang, Ling,Xu, Hongjiang,Geng, Wenjun,Gao, Yong,Xia, Chunguang,Zhang, Xiquan,Meng, Qingyi,Wu, Donghai,Zhao, Junling,Hu, Wenhui
supporting information, p. 2744 - 2748 (2015/06/08)
A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50 = 1.9 nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile.
Synthesis of functionalized aryl fluorides using organolithium reagents in flow microreactors
Nagaki, Aiichiro,Uesugi, Yuki,Kim, Heejin,Yoshida, Jun-Ichi
supporting information, p. 705 - 708 (2013/05/08)
Flow on: Flow microreactors enable the generation of aryl lithium compounds and subsequent electrophilic fluorination with NFSI and N-fluorosultam. The reaction can be successfully accomplished to synthesize various aryl fluorides involving an electron-withdrawing, an electron-donating, and a sterically hindered functional group in good yields. Copyright
PYRIDINE COMPOUNDS AND THE USES THEREOF
-
Page/Page column 293, (2012/04/04)
The invention relates to substituted pyridine compounds of Formula (I) and the pharmaceutically acceptable salts, prodrugs, and solvates thereof, wherein R1a, A1, A2, E, G, Z1, and Z2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.
Gold-catalyzed direct arylation
Ball, Liam T.,Lloyd-Jones, Guy C.,Russell, Christopher A.
, p. 1644 - 1648,5 (2020/08/24)
Biaryls (two directly connected aromatic rings, Ar1-Ar 2) are common motifs in pharmaceuticals, agrochemicals, and organic materials. Current methods for establishing the Ar1-Ar2 bond are dominated by the cross-coupling of aryl halides (Ar1-X) with aryl metallics (Ar2-M). We report that, in the presence of 1 to 2 mole percent of a gold catalyst and a mild oxidant, a wide range of arenes (Ar1-H) undergo site-selective arylation by arylsilanes (Ar 2-SiMe3) to generate biaryls (Ar1-Ar 2), with little or no homocoupling (Ar1-Ar 1/Ar2-Ar2). Catalysis proceeds at room temperature and tolerates a broad range of functional groups, including those incompatible with cross-coupling. These features expedite biaryl preparation, as demonstrated by synthesis of the nonsteroidal anti-inflammatory diflunisal.
Synthesis of 18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene
Steiniger, Bjoern,Wuest, Frank R.
, p. 817 - 827 (2007/10/03)
The SUZUKI reaction of organoboron compounds with 4-[18F] fluoroiodobenzene has been developed as a novel radiolabelling technique in 18F chemistry. The cross-coupling reaction of p-tolylboronic acid with 4-[18F]fluoroiodobenzene was used to screen different palladium complexes, bases and solvents. Optimized reaction conditions (Pd 2(dba)3, Cs2CO3, acetonitrile, 60°C for 5 min) were further applied to the synthesis of various 18F-labelled biphenyls bearing different functional groups. The reaction proceeded in excellent radiochemical yields of up to 94% within 5 min while showing good compatibility to many functional groups. Copyright
Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes
Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 15292 - 15293 (2007/10/03)
Arene and phenylmethanesulfonyl chlorides can be cross-coupled with aryl, heteroaryl, and alkenylstannanes with desulfitation in the presence of 10 mol % CuBr·Me2S, 1.5 mol % Pd2dba3, and 5 mol % tri-2-furylphosphine in tetrahydrofuran or toluene under reflux. This extension of the Stille cross-coupling reaction realizes a new and economical method for the generation of C?C bonds. The palladium-catalyzed carbonylative Stille cross-coupling reactions of arenesulfonyl chlorides and organostannanes in the presence of CO (60 bar) at 110 °C in toluene generate the corresponding ketones. Arenesulfonyl chlorides are more reactive than aryl chlorides and aryl bromides in their Stille cross-coupling with organostannanes but less reactive than aryl iodides. The new methods disclosed for the generation of C?C bonds open new possibilities for medicinal chemistry and material sciences. Copyright
