Tag: 200-300

Development of a Convergent Large-Scale Synthesis for Venetoclax, a First-in-Class BCL-2 Selective Inhibitor was written by Ku, Yi-Yin;Chan, Vincent S.;Christesen, Alan;Grieme, Timothy;Mulhern, Mathew;Pu, Yu-Ming;Wendt, Michael D.. And the article was included in Journal of Organic Chemistry in 2019.HPLC of Formula: 179232-29-2 This article mentions the following:

The process development of a new synthetic route leading to an efficient and robust synthetic process for venetoclax (1: the active pharmaceutical ingredient (API) in Venclexta) is described. The redesigned synthesis features a Buchwald-Hartwig amination to construct the core ester 23c (2 tert-Bu ester) in a convergent fashion by connecting two key building blocks (4c and 26), which is then followed by a uniquely effective saponification reaction of 23c using anhydrous hydroxide generated in situ to obtain 2. Finally, the coupling of the penultimate core acid 2 with sulfonamide 3 furnishes drug substance 1 with consistently high quality. The challenges and solutions for the key Pd-catalyzed C-N cross-coupling will also be discussed in detail. The improved synthesis overcomes many of the initial scale-up challenges and was accomplished in 46% overall yield from 3,3-dimethyldicyclohexanone (6), more than doubling the overall yield of the first generation route. The new process was successfully implemented for producing large quantities of 1 with >99% area purity. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2HPLC of Formula: 179232-29-2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.HPLC of Formula: 179232-29-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Benzocyclo闁哄鐡璽atetraenes. IV. 1,2,3,4,5,6-Tribenzo-闁?sup>1,3,5,7-cyclo闁哄鐡璽atetraene was written by Shuttleworth, R. G.;Rapson, W. S.;Stewart, E. T.. And the article was included in Journal of the Chemical Society in 1944.COA of Formula: C10H11BrO2 This article mentions the following:

Tetraphenylene (I) (3 g.) in 200 cc. AcOH at 80-90闁? treated with 7 g. CrO₃ in 7 cc. H₂O and 50 cc. AcOH during 2 h., gives 0.6 g. unchanged I and 0.6 g. of 1,2,3,4,5,6-tribenzo-1,3,5,7-cyclo闁哄鐡璽atetraene-7,8-dicarboxylic anhydride (II), deep yellow, m. 228-9闁? 0.1 g. 闁?diphenylbenzene-2′,2”-dicarboxylic acid (III), m. 262.5-3.5闁? was isolated also; III seps. with 2 mols. of AcOH, lost at 150闁? The Na salt from II is stable to KMnO₄ and II in AcOH gives III with CrO₃ only at 100闁? II is not decarboxylated by refluxing in quinoline with Cu dronze but pyrolysis of 0.5 g. of II with Ba(OH)₂ at about 300闁?gives 0.15 g. of 1,2,3,4,5,6-tribenzo-1,3,5,7-cyclooctatetraene (IV), m. 138.5-9闁? which is stable to KMnO₄ in Me₂CO. IV and Br in CCl₄ give the 7,8-dibromide, light yellow, m. 155-6闁? Hydrogenation of IV with reduced PtO₂ gives 1,2,3,4,5,6-tribenzo-1,3,5-cyclo闁哄鐡璽atriene, m. 111-13闁? 2-O₂NC₆H₄C₆H₄CO₂H-2 (68% yield) does not yield an alkali-soluble product on reduction with FeSO₄ and NH₄OH or Ba(OH)₂. 2-O₂NC₆H₄C₆H₄Me2 (37% yield) with Sn and HCl gives 83% of the 2-NH₂ derivative, which yields 63% of the 2-I derivative; oxidation with KMnO₄ results in extensive degradation of the nucleus and CrO₃ gives only 23% of 2-IC₆H₄C₆H₄CO₂H-2 (V). 闁?C₆H₄I₂ (37% yield) (50 g.) and 20 g. 闁?IC₆H₄CO₂Et with 15 g. Cu bronze at 280-5闁? followed by hydrolysis, give 8.5 g. of V; the Et ester (VI) b₃ 168-9闁? VI (5 g.) and 20 g. 闁?IC₆H₄CO₂Et with 10 g. Cu bronze at 320闁?give 0.5 g. III. VI and 闁?C₆H₄CH₂CO₂Et with Cu bronze at 290-5闁?yield 3,4-benzocoumarin. Et (闁?bromophenyl)acetate, b₄ 114闁? m. 35-6闁? (2-BrC₆H₄)₂, transformed into the Grignard reagent by refluxing with Mg for 36 h., HC(OEt)₃ added and the mixture refluxed for 5 h., gives 2-bromo-2′-aldehydobiphenyl (contaminated with (2-BrC₆H₄)₂, b₇ 152-7闁? (VII); 2,4-dinitrophenylhydrazone, orange-yellow, m. 217闁? semicarbazone, m. 198闁? VII, 闁?BrC₆H₄CH₂CO₂Na and AcOH, heated 12 h. at 150-60闁? give 濞?闁?bis(闁?bromophenyl)cinnamic acid, m. 186闁? its conversion into IV was not attempted. In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7COA of Formula: C10H11BrO2).

Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.COA of Formula: C10H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mechanically axially chiral catenanes and noncanonical mechanically axially chiral rotaxanes was written by Maynard, John R. J.;Gallagher, Peter;Lozano, David;Butler, Patrick;Goldup, Stephen M.. And the article was included in Nature Chemistry in 2022.Computed Properties of C8H7BrO3 This article mentions the following:

The symmetry properties of these mols. and in doing so identify a straightforward route to access them from simple chiral building blocks was re-examined This anal. also led us to identify an analogous but previously unremarked upon rotaxane stereogenic unit, which also yielded to our co-conformational auxiliary approach. With methods to access mech. axially chiral mols. in hand, their properties and applications can now be explored. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1Computed Properties of C8H7BrO3).

Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Computed Properties of C8H7BrO3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bifunctional Indenyl-Derived Receptors for Fluoride Chelation and Detection was written by Tirfoin, Remi;Abdalla, Joseph A. B.;Aldridge, Simon. And the article was included in Chemistry – A European Journal in 2015.Application In Synthesis of 3,4-Dibromoaniline This article mentions the following:

Anion receptors based on a [CpFe(indenyl)] scaffold offer the possibility for the incorporation of adjacent Lewis acidic functions onto a six-membered carbocyclic framework, while at the same time retaining the colorimetric/electrochem. reporter mechanisms available to synthetically simpler ferrocene systems. Thus, [CpFe(indenyl)] systems featuring mutually ortho BMes₂ and PPh₂Me⁺ substituents (with either 4,5 or 5,6 regiochem.) are accessible which are capable of cooperative fluoride ion fixation. Simultaneous binding at the borane and phosphonium centers can be established by spectroscopic, structural and computational approaches, and is responsible for the favorable thermodn. associated with F^– uptake. Thus, in contrast to simple BMes₂ systems, the binding of fluoride is found to be more favorable than the uptake of cyanide (which interacts only with the borane Lewis acid). Moreover, in the case of a 4-(MePh₂P)-5-(Mes₂B)-7-Me-indenyl derivative, fluoride chelation is signalled not only by a large cathodic shift in the Fe^II/Fe^III potential (>500 mV in THF), but also by a distinct color change from green (for the free receptor) to maroon for the adduct. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Application In Synthesis of 3,4-Dibromoaniline).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Application In Synthesis of 3,4-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling For C-S Formation was written by Ang, Nate W. J.;Ackermann, Lutz. And the article was included in Chemistry – A European Journal in 2021.Reference of 14425-64-0 This article mentions the following:

An efficient and mild electrochem. thiolation by cross-electrophile coupling of alkyl bromides with functionalized bench-stable thiosulfonates to access alkyl sulfides RSR¹ [R = (CH₂)₅Cl, Cy, (CH₂)₂Ph, etc.; R¹ = Cy, Ph, 2-thienyl, etc.] with excellent efficacy and broad functional group tolerance. Cyclic voltammetry and potentiostatic anal. were performed to elucidate mechanistic insights into this electrocatalytic thiolation reaction. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Reference of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Reference of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Structure-activity relationships of N²-substituted guanines as inhibitors of HSV1 and HSV2 thymidine kinases was written by Hildebrand, Catherine;Sandoli, Daniele;Focher, Federico;Gambino, Joseph;Ciarrocchi, Giovanni;Spadari, Silvio;Wright, George. And the article was included in Journal of Medicinal Chemistry in 1990.Recommanded Product: 3,4-Dibromoaniline This article mentions the following:

Guanines I [R = Ph, substituted Ph, Bu, hexyl, (CH₂)₅OH, CH₂Ph, CH₂C₆H₄Cl] were prepared and tested for inhibition of the thymidine kinases encoded by Herpes simplex viruses type 1 and type 2. Compounds with hydrophobic, electron-attracting groups in the meta position of the Ph ring such as I (R = 3-CF₃C₆H₄) were the most potent inhibitors of both enzymes. Many derivatives were significantly more potent against the type 2 thymidine kinase than against the type 1 and can effectively discriminate between the two enzymes. I [R = alkyl, (un)substituted CH₂Ph] were moderately potent inhibitors, and the type 2 enzyme was again more sensitive than the type 1 enzyme. None of the compounds inhibited the thymidine kinase isolated from the host HeLa cell line, suggesting that members of this class of compounds may be useful nonsubstrate, antiviral compounds for latent herpesvirus infections. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Recommanded Product: 3,4-Dibromoaniline).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Recommanded Product: 3,4-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of quinoline-based NNN-pincer nickel(II) Complexes: a robust and improved catalyst system for C-H bond alkylation of azoles with alkyl halides was written by Patel, Ulhas N.;Pandey, Dilip K.;Gonnade, Rajesh G.;Punji, Benudhar. And the article was included in Organometallics in 2016.HPLC of Formula: 57293-19-3 This article mentions the following:

The quinoline-based pincer nickel(II) complexes I (2a,b, X = Cl, R = Me, Et; 3a,b, X = Br, R = Me, Et; 4a, X = OAc, R = Me) were prepared by the reaction of the ligand precursors N-[(2-dialkylamino)phenyl]-8-quinolinamines with (DME)NiCl₂ (THF)₂NiBr₂ or Ni(OAc)₂ in the presence of Et₃N. All of these complexes were characterized by ¹H and ¹³C NMR spectroscopy as well as by elemental anal. Further, the mol. structures of 2a and 3a,b were elucidated by x-ray crystallog. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles in 2-position with various unactivated alkyl halides containing 閻?hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3HPLC of Formula: 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.HPLC of Formula: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Protein Structure-Based Design, Synthesis, and Biological Evaluation of 5-Thia-2,6-diamino-4(3H)-oxopyrimidines: Potent Inhibitors of Glycinamide Ribonucleotide Transformylase with Potent Cell Growth Inhibition was written by Varney, Michael D.;Palmer, Cindy L.;Romines, William H. III;Boritzki, Theodore;Margosiak, Stephen A.;Almassy, Robert;Janson, Cheryl A.;Bartlett, Charlotte;Howland, Eleanor J.;Ferre, Rosanne. And the article was included in Journal of Medicinal Chemistry in 1997.Product Details of 38239-45-1 This article mentions the following:

The design, synthesis, biochem., and biol. evaluation of a novel series of 5-thia-2,6-diamino-4(3H)-oxopyrimidine inhibitors of glycinamide ribonucleotide transformylase (GART) are described. The compounds were designed using the X-ray crystal structure of human GART. The monocyclic 5-thiapyrimidinones were synthesized by coupling an alkyl thiol with 5-bromo-2,6-diamino-4(3H)-pyrimidinone. The bicyclic compounds were prepared in both racemic and diastereomerically pure forms using two distinct synthetic routes. The compounds were found to have human GART K_is ranging from 30 婵炴挾鎷?to 2 nM. The compounds inhibited the growth of both L1210 and CCRF-CEM cells in culture with potencies down to the low nanomolar range and were found to be selective for the de novo purine biosynthesis pathway. The most potent inhibitors had 2,5-disubstituted thiophene rings attached to the glutamate moiety. Placement of a Me substituent at the 4-position of the thiophene ring resulted in inhibitors with significantly decreased mFBP (human folate-binding protein) affinity. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-methylthiophene-2-carboxylic acid (cas: 38239-45-1Product Details of 38239-45-1).

5-Bromo-3-methylthiophene-2-carboxylic acid (cas: 38239-45-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Product Details of 38239-45-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air was written by Bose, Shubhankar Kumar;Brand, Simon;Omoregie, Helen Oluwatola;Haehnel, Martin;Maier, Jonathan;Bringmann, Gerhard;Marder, Todd B.. And the article was included in ACS Catalysis in 2016.Synthetic Route of C10H13BrO This article mentions the following:

A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B₂pin₂) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlorides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Synthetic Route of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Aminobenzothiazoles. XI. Synthesis of 5,4′-disubstituted 1-anilinobenzothiazoles from nuclear substituted thiocarbenilides was written by Dyson, George M.;Hunter, Robert F.;Soyka, Charles. And the article was included in Journal of the Chemical Society in 1929.Safety of 3,4-Dibromoaniline This article mentions the following:

(P-BrC₆H₄NH)₂CS and Br in CHCl₃ yield a perbromide, which, on heating, gives a hydropentabromide(I), C₁₃H₈N₂Br₂S.HBr.Br₄, orange-red needles, m. 170闁?(decomposition) and rapidly loses Br on exposure to moist air suspended in H₂SO₃ and treated with SO₂, there results 5,4′-dibromo-1-anilinobenzothiazole(II), m. 221闁? Ac derivative, m. 205-6闁? HBr salt, m. 250闁?(decomposition); Br gives I. 1-Chloro-5-bromobenzothiazole, m. 89闁? b₁₃ 157-9闁? results by heating p-BrC₆H₄NCS and PCl₅ 30-40 hrs. at 170-80闁?warming with p-BrC₆H₄NH₂ gives II. p-BrC₆H₄NHCSNHPh and Br in CHCl₃ give the hydrotribromide, m. 148闁?(decomposition), which is reduced to 4′-bromo-1-anilinobenzothiazole (III), m. 214-5闁? also obtained from 1-chlorobenzothiazole and p-BrC₆H₄NH₂. Bromination of III gives II. 1-Anilinobenzothiazole yields a hexabromide, m. 140闁? which yields II on being dissolved in boiling absolute EtOH. Hugershoff’s dibromoanilinobenzothiazole (Ber. 36, 3121(1903)) appears to consist mainly of II, although the m. p. could not be raised above 200闁? Bromination of II gives an unstable orange hexabromide, m. 254闁? which gives with hot absolute EtOH a tetra-Br substitution derivative, m. 196-8闁? (p-ClC₆H₄NH)₂CS and Br in CHCl₃ yield a hydrotribromide, orange, m. 165-7闁?(decompm); reduction gives 5,4′-dichloro-1-aminobenzothiazole, m. 224闁? Ac derivative, m. 186-7闁? HBr salt. yellow, m. 217闁? hexabromide, orange, m. 263闁?(decomposition). p-ClC₆H₄NHCSNHPh yields a Br addition compound, orange, m. 130闁?(decomposition); 4′-chloro-1-anilinobenzothiazole, m. 196闁? this is also obtained from 1-chlorobenzothiazole and p-ClC₆H₄NH₂. (p-IC₆H₄NH)₂CS and Br in CHCl₃ yield a red bromide, m. 185闁? and a yellow, m. 211闁? both, on reduction, yield 5,4′-diiodo-1-anilinobenzothiazole, m. 193闁?(decomposition); this also results by treating 1-anilinobenzothiazole in AcOH with ICl, warming the solution and diluting with H₂O. (p-FC₆H₄NH)₂CS gives a hydrotribromide, orange, m. 150-2闁?(decomposition); 5,4′-difluoro-1-anilinobenzothiazole, m. 227-8闁? 5,4′-Dinitro-1-anilinobenzothiazole, brilliant yellow, in. 280闁? this also results on nitration of 1-anilinobenzothiazole. (p-NCC₆H₄NH)₂CS and Br give an addition product, golden, m. 159-60闁?(decomposition): 5,4′-dicyano-1-anilinobenzothiazole, m. 222闁? (p-EtO₂CC₆H₄NH)₂CS yields a hydropentabromide, orange, m. 110闁?(decompn); reduction gives Et 1-anilinobenzothiazole-5,4′-dicarboxylate, m. 190-2闁? hydrolysis gives the free acid, does not m. 290闁? (p-MeOC₆H₄NH)₂CS yields a brick-red bromide, m. 137闁?(decomposition), reduced to a dibromo-5,4′-dimethoxy-1-anilinobenzothiazole, m. 240闁? PhNHCSNAcPh yields a hydrotribromide, orange, m. 167闁?(decomposition); the same compound is obtained from 1-acetanilinobenzothiazole, HBr and Br (Hugershoff, Ber. 36, 3136(1903)); Br in CHCl₃ gives an orange hexa-Br addition compound, m. 163闁?(decomposition). In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Safety of 3,4-Dibromoaniline).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Safety of 3,4-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary