Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 51329-15-8, name is Methyl 3,5-dibromobenzoate, 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 51329-15-8, category: esters-buliding-blocks

a) 3-Bromo-5-hydroxy-benzoic acid methyl ester. A 5 mL tube was charged with 3,5-dibromo-benzoic acid methyl ester (586 mg, 2.0 mmol), bis(pinacolato)diboron (254 mg, 1.0 mmol), potassium acetate (294 mg, 3.0 mmol) and PdCl2(dppf) complex (50 mg). DMSO (3 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 80 C., the mixture was diluted with ethyl acetate (10 mL) and extracted with brine (10 mL, three times), and saturated aqueous sodium bicarbonate (5 mL), and the organic layer was dried and concentrated to give 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester. To a solution of this material in acetone (4 mL) was added an aqueous solution of Oxones (2 KHSO5.KHSO4.K2SO4) (1.23 g in 5 mL water), and the reaction mixture was stirred vigorously for 8 min at room temperature. The reaction mixture was quenched with aqueous sodium hydrogensulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine and water, dried and concentrated. The residue was passed through a short silica gel column using a gradient of methylene chloride to 2% methanol in methylene chloride as an eluent to give 104 mg of 3-bromo-5-hydroxy-benzoic acid methyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,5-dibromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Locus Pharmaceuticals, Inc.; US2008/280891; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6279-86-3, name is Triethyl methanetricarboxylate, 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 6279-86-3, SDS of cas: 6279-86-3

Example IEthyl 2,4-dihvdroxy-7,7-dimethyl-5-oxo-5,6,7,8-tetrahvdroquinoline-3-carboxylate10 g 3-Amino-5,5-dimethyl-2-cyclohexen-1 -one and 25 g 2-Ethoxycarbonyl-malonic acid diethyl ester are combined and heated for 10 minutes at 210C (bath temperature).Thereafter the mixture is cooled to room temperature and triturated with diethylether. The crystalline precipitate is collected by filtration and dried in vacuo.Yield: 9,9 g (49 % of theory)Mass spectrometry (ESI+): m/z = 280 [M+H]+ Rf-value: 0,45 (silica gel, dichloromethane/methanol 9:1 )

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WAGNER, Holger; BERTA, Daniela; FUCHS, Klaus; GIOVANNINI, Riccardo; HAMPRECHT, Dieter, Wolfgang; KONETZKI, Ingo; STREICHER, Ruediger; TRIESELMANN, Thomas; WO2011/101424; (2011); A1;,
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Reference of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Acetylenedicarboxylic acid (0.35 g, 3.09 mmol, 1.0 eq.) was dissolved in NMP (10 mL) and cooled to 0 C, to which compound 34 (2.06 g, 7.43 mmol, 2.4 eq.) was added, followed by DMTMM (2.39 g, 8.65 mmol, 2.8 eq.) in portions. The reaction was stirred at 0 C for 6 h and then diluted with ethyl acetate and washed with water and brine. The organic solution was concentrated and triturated with a mixture solvent of ethyl acetate and petroleum ether. The solid was filtered off and the filtrate was concentrated and purified by column chromatography (80-90% EA/PE) to give a light yellow oil (2.26 g, >100% yield), which was used without further purification. MS ESI m/z [M+H]+ 633.30.

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, tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANGZHOU DAC BIOTECH CO, LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; GAI, Shun; YE, Hangbo; YANG, Chengyu; GUO, Huihui; ZHOU, Xiaomai; XIE, Hongsheng; TONG, Qianqian; CAO, Minjun; ZHAO, Linyao; JIA, Junxiang; LI, Wenjun; ZUO, Xiaotao; LIN, Chen; XU, Yifang; GUO, Zixiang; (274 pag.)WO2017/46658; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

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. 120974-97-2, name is (E)-Methyl 2-(methoxyimino)-2-(o-tolyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H13NO3

To the solution of IV (5 g, 24.0 mmol) in CCl4 (150 mL) was added NBS (4.7 g, 26.4 mmol) andBPO (1 g, 4.13 mmol). The reaction mixture was heated to reflux until the starting material had beencompletely consumed as judged by TLC. The precipitate was filtered off, and the solvent wasevaporated under reduced pressure. The residue was purified by a silica-gel column chromatography(petroleum ether/EtOAc = 15:1) to give (E)-methyl 2-(2-(bromomethyl)phenyl)-2-(methoxyimino)-acetate (V). Yield 85%; Yellow oil; 1H-NMR (CDCl3) delta 7.47-7.13 (m, 4H, Ar-H), 4.32 (s, 2H, CH2),4.04 (s, 3H, OCH3), 3.85 (s, 3H, OCH3). Anal. calcd for C11H12BrNO3: C 46.18, H 4.23, N 4.90; foundC 46.32, H 4.21, N 4.88.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 120974-97-2.

Reference:
Article; Liu, Yuanyuan; Li, Yi; Chen, Nanqing; Lv, Kunzhi; Zhou, Chao; Xiong, Xiaohui; Li, Fangshi; Molecules; vol. 19; 6; (2014); p. 8140 – 8150;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 653-92-9

To a mixture of methyl 2-bromo-4-fluorobenzoate (10.1 g, 43.34 mmol, 1.00 equiv) in THF (100 ml) with Cs2C03 (42 g, 128.91 mmol, 3.00 equiv) and Pd(dppf)CI2 (3.5 g, 4.78 mmol, 0.1 1 equiv) was added Et3B (1 M in tetrahydrofuran) (65 ml, 65 mmol, 1.50 equiv). The reaction mixture was stirred overnight at 80C. Water was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :30 EA/PE) to yield methyl 2-ethyl-4- fluorobenzoate as a yellow oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Ester – Wikipedia,
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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. 62451-84-7, name is Methyl 2-(3-(trifluoromethyl)phenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 2-(3-(trifluoromethyl)phenyl)acetate

To a stirred solution of methyl 2-[3-(trifluoromethyl)phenyl]acetate (6.33 g, 29 mmol) in DMF (45 mL) at 0C was added NaH (60%, 1.28 g, 31.9 mmol). The reaction mixture was stirred for 1 hour and then canuulated drop wise into a solution of 2-(4-bromobutoxy)tetrahydropyran (6.88 g, 29 mmol) in DMF (45 mL) also at 0C. The reaction was further stirred at RT for one hour and poured onto an aqueous saturated solution of NH4C1. The product was extracted with EtOAc, and the combined organic phase was dried over Na2S04 and concentrated under vacuo. A column chromatography (Si02, Heptane / EtOAc) gave 7.82 g (72%) of methyl 6-tetrahydropyran-2- yloxy-2-[3-(trifluoromethyl)phenyl]hexanoate as a light yellow oil.

According to the analysis of related databases, 62451-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; SARIE, Jerome Charles; VASTAKAITE, Greta; (61 pag.)WO2018/83050; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Application of 29823-21-0, These common heterocyclic compound, 29823-21-0, name is Ethyl 8-Bromooctanoate, 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.

EXAMPLE 73 Ethyl 8-(4,5-diphenyl-2-oxo-2,3-dihydroimidazol-1-yl)octanoate 4,5-Diphenylimidazol-2-one was treated with ethyl 8-bromooctanoate and potassium carbonate in butanone to give after work-up the title compound, m.p. 78-79 C., Found:C, 73.7;H, 7.4;N, 6.7%;C25 H30 N2 O3 requires: C, 73.9;H, 7.4;N, 6.9%

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; The Johns Hopkins University; US5648373; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 29547-04-4, name is Methyl 2,4-dibromobutanoate, 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. Safety of Methyl 2,4-dibromobutanoate

A solution of N;,N2-dibenzylethane- 1 ,2-diamine (1.0 eq), methyl 2,4-dibromobutanoate (1.1.0 eq) and Et3N (3.0 eq) in DCM (0.77 M) was stirred in a sealed tube at 60 C fo 16 h. The mixture was diluted with DCM, washed with sat. aq. NaHC03, brine, dried and concentrated. The residue was purified by flash chromatography (petroleum ether/EtOAc from 90: 10 to 0: 100) to give the title compound (57%) as an oil. MS (ES+) m/z 339 (M+H)+.

The synthetic route of Methyl 2,4-dibromobutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRBM SCIENCE PARK S.P.A.; C.N.C.C.S. S.C.A.R.L. COLLEZIONE NAZIONALE DEI COMPOSTI CHIMICI E CENTRO SCREENING; BIANCOFIORE, Ilaria; CIAMMAICHELLA, Alina; FERRIGNO, Federica; HARPER, Steven; MALANCONA, Savina; ONTORIA ONTORIA, Jesus Maria; PAONESSA, Giacomo; PONZI, Simona; SUMMA, Vincenzo; (143 pag.)WO2018/115275; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 169044-96-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 169044-96-6 name is Methyl 2-amino-5-bromo-4-methoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 3: 6-Bromo-7-methoxyquinazoiine-2,4( lH,3H)-dioneTo a stirred suspension of methyl 2-amino-5-bromo-4-methoxybenzoate (5.5 g, 0.021 mol) in acetic acid (25 mL) was added 0.1 M aqueous solution of potassium cyanate (7.49 g, 0.10 mol) dropwise at room temperature. The reaction mixture was stirred at 50C for 24 h. The solid separated was filtered, washed with water (20 mL) followed by 10% EtOAc in hexane (50 mL) and dried under vacuum to afford the corresponding urea.To the stirred suspension of the above urea in methanol (20 mL) was added 2N sodium hydroxide (10 mL). The reaction mixture was stirred at 90C for 1 h. The mixture was cooled to room temperature, acidified with 3M hydrochloric acid to pH 3. The solid obtained was filtered and dried under vacuum to afford the title compound as white solid (3.5 g, 61% yield). *H NMR (400 MHz, DMSO-d6) : delta 11.29 (s, 1H), 11.18 (S, 1H), 7.94 (S, 1H), 6.74 (s, 1H), 3.90 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-bromo-4-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 25542-62-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25542-62-5 name is Ethyl 6-bromohexanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Reactions were carried out in a Biotage Initiator 60 Microwave Reactor, employing the 20mL process-scale reactor vials. Thirteen (13) identical reactions at the 10 mmol scale were setup in parallel and processed in serial, as follows: All three (3) reagents and reaction solvent were added to the MW vial in the following sequence; (1) ethyl-bromo-hexanoate (1.77 mL), (2) salicylaldehyde (1.05 mL), (3) cesium carbonate (CS2CO3) (3.91 g) and (4) reaction solvent DMA (17.18 mL). Care was taken to dispense the N-N-dimethylacetamide (DMA) solvent in such a manner so as to wash down the vial walls of reactant or solid base. To each vial was added a magnetic stir bar and fitted with a crimp seal cap and adapter collar. The reactions were than process in the MW Reactor for 10 minutes (at temperature) at 140 C with mixing. Following standard ramp up, fixed hold time at temperature and cool down, samples were kept sealed at ambient temperature until the entire lot was processed. The reaction mixtures were combined and transferred to a 2L separatory funnel. Vial contents were washed with ethyl acetate (EtOAc), and a total EtOAc layer of about 800 mL was added. To this was added 800 mL of 1.0 N NaOH solution, and the two layers were vigorously shaken and mixed and then separated. The NaOH aqueous layer was back-extracted 3 x 250 mL with EtOAc, and all the organic layers were combined (about 750 mL) and washed with 800 mL of 1.0 M citric acid solution. The citric acid layer was again back extracted with EtOAc (3 x 250 mL), and the organic layers were again combined (about 1.5 L) and washed (3 x 500 mL) with brine (saturated NaCl), dried over sodium sulfate (Na2SO t) and concentrated to dryness in vacuo. Silica gel TLC (3: 1 Hexanes-EtOAc) Rf = 0.34 (product), Rf = 0.45, 0.25 (trace impurities). Theoretical yield = 13 x 2.64 g or 34.32 g (130 mmol). Isolation and Observed yield = 33.30 g, (33.30 g/34.32 g x 100) = 97%. NMR (, 13C, COSY) and LCMS (ESI+/-) conform to structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-bromohexanoate, and friends who are interested can also refer to it.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.; WO2014/165827; (2014); A1;,
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Ester – an overview | ScienceDirect Topics