Category: esters-buliding-blocks

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 10601-80-6

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL×3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Reference of 653-92-9, These common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Treat a solution of l-vinylpyrrolidin-2-one (2 g, 8.58 mmol) in dry THF (30 mL) with lithium diisopropylamide (LDA) (13 mL, 31.45 mmol) at -20 0C under N2 atmosphere and stir at the same temperature for 30 min. Then add methyl 2-bromo-4- fluorobenzoate (2 g, 8.58 mmol) and stir it over the weekend. Add an HCl (12 N, 9 mL) solution and water (12 mL). Remove the THF and add HCl (12 N, 12 mL) and water (15 mL). Heat it to 100 0C for 15 h. Cool the mixture to RT and add a 5 % NaOH solution. Extract the solution with ether, dry over magnesium sulfate, and remove the solvent. Purify the residue by column chromatography (hexane to ethyl acetate) to give the title compound (0.42 g, 27 %). MS (ES) m/z 244 [M+l]+.

The synthetic route of 653-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 924-99-2

N-[2-methoxyl-4[4-(dimethyl amino)piperid-1-yl]aniline]guanidine (II) (2.9 g, 10 mmol), N,N-dimethylaminoethyl acrylate (2.0 g, 14.0 mmol) and N,N-dimethylformamide 30 mL were added in a reaction bottle, were heated to a temperature of 115-125 C., and were subjected to stirring reaction for 22-24 hours to finish TLC detection reaction. Concentration under reduced pressure was carried out, obtained residues were added with 50 mL of ethanol, and were cooled to room temperature while stirring, and then solid was separated out. The solid was filtered, a filter cake was washed with cold ethanol, and was dried under vacuum to obtain off-white solid N2-[4-[4-(dimethyl amino)-1-piperidyl]-2-methoxyphenyl]amino-4(1H)-pyrimidone (III) 2.73 g, the yield was 79.6%, and FAB-MS m/z: 344 [M+H]+.

According to the analysis of related databases, 924-99-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUZHOU MIRACPHARMA TECHNOLOGY CO., LTD.; Xu, Xuenong; (7 pag.)US10039775; (2018); B2;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H11NO3

A mixture of l -amino-3-[tert-butyl (dimethyl) silyl] oxy-5-cyclopropyl-pyrrolidin-2-one (10.5 g, 38.83 mmol) and ethyl 2-ethoxy-2-imino-acetate (14.1 g, 97.06 mmol) in ethanol (150 mL) was stirred at 90 C for 12 h and concentrated under reduced pressure to afford crude ethyl 2-[[3-[tert- butyl (dimethyl) silyl] oxy-5-cyclopropyl-2-oxo-pyrrolidin-l-yl] amino]-2-imino-acetate (10.0 g, 70%) as a yellow oil. LCMS RT = 0.804 min, m/z =370.2 [M + H]+. LCMS (5 to 95% acetonitrile in water + 0.03%o trifluoacetic acid over 1.5 mins) retention time 0.804 min, ESI+ found [M+H] =370.2.

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A 2.5 M solution of n-BuLi in hexane (2.04 mL, 5.10 mmol, 1.02 equiv) is added dropwise to a solution of diisopropylamine (0.74 mL, 5.25 mmol,1.05 equiv) in anhydrous THF (5 mL) at -78 C under Ar atmosphere and thereaction mixture is allowed to stir for 30 min at -78 C. After stirring an additional 30 min at -5 C, a solution of methyl 2,2-diphenylacetate (1.13 g, 5.00 mmol,1.00 equiv) in anhydrous THF (2 mL) is added dropwise at -78 C, and the reaction mixture is allowed to stir for 10 min. Finally, crotyl bromide (trans, 85% pure; 810 mg,6.00 mmol, 1.20 equiv) is added dropwise at -78 C and the mixture is slowly warmed to rt. After stirring for 16 h at rt, the reaction mixture is cooled to 0 C, quenched by the addition of saturated aq. NH4Cl (10 mL) then extracted with Et2O (4 × 10 mL). The combined organic extracts are washed with brine, dried overanhydrous Na2SO4, filtered and concentrated under reduced pressure; yield: 1.00 g, 3.57 mmol, 71%, yellow liquid. The product is obtained as inseparable mixture of E/Z isomers (90:10; cf. NMR spectra).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl Diphenylacetate, its application will become more common.

Reference:
Article; Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander; Synthesis; vol. 50; 19; (2018); p. 3875 – 3885;,
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Related Products of 54335-33-0, These common heterocyclic compound, 54335-33-0, name is Methyl 2,4-dibromobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of benzoic acid methyl ester (3, 4a,b) (500 mg), the respective arylamine compounds (2.4 equiv for 3, 1.2 equiv for 4a,b), Cs2CO3 (2.8 equiv for 3, 1.4 equiv for 4a,b), BINAP (0.08 equiv) in 1,4-dioxane (5 mL) was added Pd(OAc)2 (5 mol percent) under nitrogen. And the reaction mixture was stirred at 100 °C for 10?24 h. The reaction mixture was cooled to room temperature, and then H2O was added. The mixture was extracted with ethyl acetate, and then the organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography.

The synthetic route of 54335-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Chao; Lin, Kai; Huang, Lan; Pan, Wei-Dong; Liu, Sheng; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2490 – 2494;,
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Application of 69812-51-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 69812-51-7 as follows.

General procedure: To a solution of compound 7 (400mg, 1.0 eq) in CH2Cl2 or MeCN (30mL), the substituted benzenesulfonyl chloride (1.2 eq), K2CO3 (3.5 eq) were added and stirred at room temperature overnight. After reaction completed, the solvent was removed under reduced pressure and the residue was dissolved with ethyl acetate, washed by brine, dried, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluents and then acidized with 2N HCl/Et2O (1mL) to give the title compounds (8a-h).

According to the analysis of related databases, 69812-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Xin-Yue; Li, Yu-Huan; Tang, Sheng; Zhang, Xin; Wang, Yan-Xiang; Wang, Sheng-Gang; Jiang, Jian-Dong; Li, Ying-Hong; Song, Dan-Qing; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 133 – 142;,
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Application of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; YALE UNIVERSITY; WO2008/70823; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 24393-53-1, category: esters-buliding-blocks

Example 1; 4′-((1S.2SV2-ir(2S)-2-MethylPyrrolidin-1-v?methyllcvcloproDvn-1.1′-biphenyl-4- carbonitrile; Example 1A; fra/7S-3-(4-Bromophenyl) prop-2-en-1 -ol; To a solution of ethyl trans-4-bromocinnamate (8 ml_, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C dropwise. After the addition, the mixture was allowed to warm from -78 0C to -30 0C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried withMgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz1 1H)1 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz, J =3 Hz, 1H), 7.25 (d, J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.; Example 26; 4′-(f1R.2S)-2-(2-ff2R)-2-Methylpyrrolidin-1-yl1ethyl>cvclopropyh-1.1′-biphenyl-4- carbonitrile; Example 26A; 3-(4-BromophenvQprop-2-ene i-p|; To a solution of ethyl trans-4-bromocinnamate [CAS 24393-53-1] (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added dropwise diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C. Following the addition, the mixture was allowed to warm from -780C to -300C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added. The organic layer was separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz, 1 H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt. J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz1 J =3 Hz, 1H), 7.25 (d. J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H); Example 34; 2-r4-((1S.2S)-2-(f(2S)-2-MethylPyrrolidin-1-yllmethyl)cvclopropyhphenyllPyridazin- 3(2H)-one; Example 34A; (E)-3-(4-bromophenyl)prop-2-en-1-ol; To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (25 g, 96 mmol) inDCM (300 ml) under nitrogen and cooled to -78 0C was added dropwise DIBAL-H (240 ml, 1 M in DCM, 240 mmol) in about 20 minutes. The mixture was stirred at -780C for 2 hours. Then, the dry ice bath was removed. The reaction was diluted with DCM (500 ml_), quenched with HCI (1N), and partitioned. The combined organic phases were washed with HzO, dried and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.43 (t, J = 6 Hz1 1H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz, 1H), 6.57 (d, J =15 Hz, 1H), 7.25 (d, J = 9 Hz, 2H)1 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 3-(4-bromophenyl)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/150010; (2007); A2;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 927-68-4, name is 2-Bromoethyl acetate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 927-68-4

In a 40 mL reaction vial under nitrogen gas, was added (1977) 2-amino-5-bromopyridin-3-ol (0.320 g, 1.693 mmol) and DMF (5 mL). The mixture was cooled to 5 C and NaH (0.102 g, 2.54 mmol) was added. The reaction mixture was stirred at 5 C for 1 hour. Next, 2-bromoethyl acetate (0.283 mL, 2.54 mmol) was introduced neat via a syringe. The reaction mixture was stirred at 5 C and slowly warmed to room temperature overnight. The mixture was cooled to 5 C and carefully diluted with water. Ethyl acetate was added and the mixture was transferred to a separatory funnel. The layers were separated and the organics were washed with brine, dried over sodium sulfate, filtered and concentrated to afford (1978) 2-((2-amino-5-bromopyridin-3-yl)oxy)ethyl acetate as a tan oil (0.45 g, 97%). LC-MS: M+1= 275/277, rt = 0.52 min, [Al].

According to the analysis of related databases, 927-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; LOMBARDO, Louis J.; MACOR, John E.; MUSSARI, Christopher P.; PASUNOORI, Laxman; RATNA KUMAR, Sreekantha; SHERWOOD, Trevor C.; POSY, Shoshana L.; SISTLA, Ramesh Kumar; HEGDE, Subramaya; RAMACHANDRA, Anupama; (425 pag.)WO2018/5586; (2018); A1;,
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