Month: February 2021

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. 81245-24-1, name is Methyl 2-methoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H12O3

Description 43Methyl 5-bromo-4-methyl-2-(methyloxy)benzoate (D43)Methyl 4-methyl 2-(methyloxy)benzoate (may be prepared as described in Description 42; 2.51 g, 0.01 mmol) was dissolved in chloroform (40 ml) and cooled to 0C. Bromine (0.72 ml, 13.97 mmol) was added dropwise over 5 minutes. The solution was stirred for one hour, then saturated aqueous sodium sulfite solution (20 ml) was added and the organic layer separated, dried (MgS04) and the solvent removed in vacuo to give the title compound as a white solid. 2.96 g.MS (electrospray): m/z [M+H]+ 259 /261

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 81245-24-1.

Reference:
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
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Application of 6065-82-3, A common heterocyclic compound, 6065-82-3, name is Ethyl diethoxyacetate, molecular formula is C8H16O4, 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 6An ethyl ester compound according to formula Illb1 wherein Q = OEt (10,11-dihydro- 5H-benzo[e]pyrido[2,3-b]azepine-10-carboxylic acid ethyl ester ) was prepared as described below.A mixture of 2-amino-3-benzylpyridine (2.1 g, 11.4 mmol) and ethyl 2,2-diethoxyacetate (3.8 g, 21.6 mmol, 1.9 eq.) in a 250 ml round-bottomed flask was treated at room temperature with concentrated sulphuric acid (10 ml) by quick addition while stirring. A vigorous exothermic reaction took place. After stirring for 30 minutes the dark mixture was poured on ice water (100 ml). Concentrated ammonia (25% aq.; 25 ml) was added to basify the mixture. Extraction with ethyl acetate (2 x 50 ml). The combined organic layers were dried with Na2SO4. Evaporation under vacuum gave 10,11-dihydro-5H- benzo[e]pyrido[2,3-b]azepine-10-carboxylic acid ethyl ester as a dark yellow oil (2.4 g, 8.9 mmol) in 79% c.y. An analytically pure sample can be obtained by chromatography on silica gel. Rf = 0.3 (EtOAc/n-heptane = 1 :1 ). Mass analysis: M+1 = 269 major peak. 1H-NMR (CDCI3) delta (ppm) 1.28 3H, d, J = 7.2 Hz, CH3; 3.80 1 H, d, J = 15.5 Hz, CHH; 4.18 1 H, d, J = 15.5 Hz, CHH; 4.32 2H, q, J = 7.2 Hz, OCH2; 5.54 1 H, d, J = 5.1 Hz; 5.86 1 H, br d, J = 5.1 Hz, NH; 6.50 1 H, dd, J = 4.8 and 7.2 Hz, ArH; 7.08 1 H, m, ArH; 7.20-7.30 4H, m, ArH; 7.88 1 H, dd, J = 1.5 Hz and 4.8 Hz, ArH.

The synthetic route of 6065-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; SEERDEN, Johannes Paulus Gerardus; WO2008/125577; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1215205-50-7, name is Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C12H13BrO2

Example 30 1-(1-{4-[1-(Ethoxycarbonyl)cyclopropyl]benzoyl}piperidin-4-yl)-3-methylpiperidine trifluoroacetic acid salt 600 mg (2.2 mmol) of ethyl 1-(4-bromophenyl)cyclopropanecarboxylate, 813 mg (4.5 mmol) of 4-(3-methylpiperidin-1-yl)piperidine, 294 mg (1.12 mmol) of molybdenum hexacarbonyl, 105 mg (0.11 mmol) of trans-bis(acetate)bis[o-(di-o-tolylphosphine)benzyl]dipalladium(II) (Herrmann’s palladacycle) and 709 mg (6.7 mmol) of sodium carbonate were suspended in 3 ml of water and heated in a microwave at 150 C. for 10 minutes. After cooling, the mixture was extracted with ethyl acetate and then filtered. The organic phase was removed from the filtrate, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC. [Reprosil C18, 10 mum, 250 mm*30 mm (50% methanol/50% water (+0.05% trifluoroacetic acid) to 70% methanol/30% water (+0.05% trifluoroacetic acid)) over a run time of 25 min]. The product-containing fractions were combined, concentrated and dried under HV. This gave 348 mg (30% of theory) of an oil. LC-MS [Method 2]: Rt=0.74 min; MS (ESIpos): m/z=399 (M-CF3COOH+H)+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.88-0.94 (m, 3H), 1.11 (t, 3H), 1.20-1.26 (m, 2H), 1.49-1.55 (m, 2H), 1.59-2.19 (m, 8H), 2.58-3.14 (m, 5H), 3.33-3.55 (m, 3H), 3.58-3.88 (m, 1H), 4.04 (q, 2H), 4.29-4.81 (m, 1H), 7.32-7.38 (m, 2H), 7.39-7.43 (m, 2H), 8.98-9.38 (m, 1H)

The synthetic route of 1215205-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 721-63-1, 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 721-63-1 as follows.

Step B: Ethyl 2-bromo-2-(4-(trifluoromethyl)phenyl)acetate To a solution of ethyl 2-(4-(trifluoromethyl)phenyl)acetate (5 g, 21.5 mmol) in CC14 (100 mL) was added NBS (11.5 g, 64.6 mmol). The resulting mixture was heated to reflux and stirred for 16 hr. The reaction mixture was then filtered and the filtrate was evaporated to dryness. The residue was purified via CombiFlash (80 g column, DCM in Petroleum ether from 0% to 30%) to give ethyl 2-bromo-2-(4-(trifluoromethyl)phenyl)acetate as an oil. NMR (CDC13, 400 MHz): 5 7.68 (d, J= 8.0 Hz, 2H), 7.63 (d, J= 8.0 Hz, 2H), 5.35 (s, 1H), 4.33-4.18 (m, 2H), 1.30 (t, J = 7.0 Hz, 3H).

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; GUIADEEN, Deodialsingh; KOTHANDARAMAN, Shankaran; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (285 pag.)WO2016/49099; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, 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 148547-19-7 as follows.

BINAP (0.67 g; 1.1 mmol; 0.05 eq.) and palladium acetate (0.24 g; 1.1 mmol; 0.05 eq.) were added to a suspension methyl 4-bromo-3-methylbenzoate (5 g; 21.8 mmol; 1 eq.), CS2CO3 (10.65 g; 32.7 mmol; 1 .5 eq.) and piperidine (2.2 g; 26 mmol; 1.2 eq.) in dioxane (100 mL) and the reaction mixture was refluxed for 15 hours. After filtration through a pad of Celite, the solution was concentrated in vacuo and the residue purified by column chromatography (petroleum ether/ethyl acetate, 80/20) to afford the title compound (4.9 g, 96%) as a brown solid.LC/MS : 233.9 (M+H)+. 1H NMR (CDCI3, 400 MHz) delta 7.84-7.82 (m, 2H), 6.99-6.97 (m, 1 H), 3.92 (s, 3H), 2.93-2.90 (m, 4H),1.76-1.67 (m, 4H, m), 1.63-1.62 (m, 2H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
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. 15012-36-9, name is Methyl 2,3-dimethylbenzoate, A new synthetic method of this compound is introduced below., name: Methyl 2,3-dimethylbenzoate

Methyl 2,3-dimethylbenzoate was dissolved in concentrated sulfonic acid (10 mL). KNO3 (808 mg, 1.2 eq.) was added to the solution at 0 C., then slowly warmed to rt overnight. The reaction was quenched with water (80 mL), extracted with ethyl acetate (2¡Á80 mL). The organic layers were evaporated to give mixture of nitrated ester and acid (1:1). The mixture was redissolved in DMF (10 mL). K2CO3 (1.1 g) and iodomethane (0.5 mL) were added to the solution. The reaction was stirred at rt for three days, then diluted with water (80 mL). It was extracted with ethyl acetate (3¡Á80 mL) and evaporated. The residue was purified by column chromatography (EtOAc in hexanes=0-30% in 45 min) to give the desired nitrobenzoate ester. 1H NMR (300 MHz, DMSO) delta 8.31 (s, 1H), 8.24 (s, 1H), 3.86 (s, 3H), 2.46 (s, 3H), 2.40 (s, 3H).

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; Rigel Pharmaceuticals, Inc.; US2012/28923; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 51760-21-5, 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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, This compound has unique chemical properties. The synthetic route is as follows.

A (2 g, 11 mmol), B (2 g, 7.4 mmol), CsF (3 g, 15 mmol) and Pd(PPh3)4 (0.2 g, 0.17 mmol) was added to a 250 mE flask. The flask was connected to Schlenk line. 200 mE 1 ,2-Dimethoxyethane was degassed and added through a canula. The flask was equipped with a water condenser and refluxed under the nitrogen for 48 hours. The solution was dried on rotary evaporator. 100 mE H20 was added and then extract with CHC13. The organic phase was evaporated to dryness and purified with chloroform through a short silica gel colunm to yield a light yellow powder 1.56 g. (Yield:62%). ?H NMR (CDC13): oe=3.97 (s, 9H), 7.90 (d, 2H), 8.06 (d, 2H), 8.44 (d, 2H) 8.49 (t, 1H).

The chemical industry reduces the impact on the environment during synthesis Dimethyl 5-bromoisophthalate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhou, Hong-Cai; Feng, Dawei; Wang, Kecheng; US2015/152123; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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 110104-60-4, COA of Formula: C6H9ClO3

General procedure: Example-115 In the same manner as in Example-12 except that cesium carbonate was used instead of potassium carbonate, from 5-chloro-4-(2,4-dichloro-5-hydroxyphenyl)-1,2-tetramethylene-4-pyrazolin-3-one and methyl (E)-4-chloro-3-methoxy-2-butenoate, methyl (E)-4-[5-(5-chloro-3-oxo-1,2-tetramethylene-4-pyrazolin-4-yl)-2,4-dichlorophenyloxy]-3-methoxy-2-butenoate was obtained with a yield of 86%. 1H-NMR (400 MHz, CDCl3): delta1.87-1.94 (m, 8H), 1.99-2.06 (m, 2H), 3.58-3.63 (m, 2H), 3.69 (s, 3H), 3.70 (s, 3H), 3.80-3.85 (m, 2H), 5.20 (s, 1H), 5.28 (s, 2H), 6.97 (s, 1H), 7.46 (s, 1H).

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; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Methyl 2-(4-bromophenyl)propanoate. To a solution of lithium diisopropylamide (2 mol/L, 22 mL, 44 mmol) in tetrahydrofuran (80 mL) was dropwise a solution of methyl 2-(4- bromophenyl)acetate (10 g, 44 mmol) in tetrahydrofuran (20 mL) at -78 C. The mixture solution was stirred for 0.5 hour at that temperature, then iodomethane (8 g, 56 mmol) was added. The mixture was stirred for 10 minutes at – 78 C, then was removed from the cooling bath and stirred for 0.5 hour. The reaction was quenched with sat. ammonium chloride, then diluted with ethyl acetate, washed with water, The organic layer concentrated to dry, purified by column chromatography (silica-gel, petroleum : ethyl acetate= 20 : 1) to give methyl 2-(4- bromophenyl)propanoate as a colorless oil (10 g, 91 %). 1H NMR (300 MHz, CDC13): delta 7.44 (d, J = 9 Hz, 2H), 7.17 (d, J = 9 Hz, 2H), 3.65-3.70 (m, 4H), 1.48 (d, J = 6 Hz, 3H).

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; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew; GAGNON, Alexandre; HARMANGE, Jean-christophe; NAVESCHUK, Christopher, G.; WO2013/75083; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, HPLC of Formula: C6H7F3O2

Bromine (18.4 mL, 357 mmol) was added dropwise over 30 minutes to a solution of commercially available (E)-ethyl 4,4,4-trifluorobut-2-enoate (50 g, 297 mmol) in carbon tetrachloride (50 mL) at room temperature under nitrogen. The resulting dark red solution was refluxed for 4 hours. Additional bromine (2ml) was added and heating was continued until the HPLC analysis showed that the starting material had been consumed. The reaction mixture was concentrated under reduced pressure to give light brown oil which used in the next step without purification. HPLC (XBridge 5mu C18 4.6×50 mm, 4 mL/min, solvent A: 10 % MeOH/water with 0.2 % H3PO4, solvent B: 90 % MeOH/water with 0.2 % H3PO4, gradient with 0-100 % B over 4 minutes): 2.96 and 3.19 minutes.

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics