Category: esters-buliding-blocks

51760-21-5, name is Dimethyl 5-bromoisophthalate, 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. Formula: C10H9BrO4

Sodium hydroxide (0.29 g, 7.32 mmol) was added to a suspension of dimethyl 5-bromoisophthalate (2 g, 7.32 mmol) in acetone (30 ml) and water (15 ml) and the reactionstirred at room temperature for 1 hour. A clear solution was achieved at this point. The reaction was stirred overnight at room temperature. The acetone was removed in vacuu and the residual solution extracted with ethyl acetate. The aqueous was then adjusted to pH4 and extracted twice with ethyl acetate. The organic was then washed with brine, dried andconcentrated to give the title compound as a 60 % pure white solid (1.23 g, 2.85 mmol, 38.9% yield). MS (m/z) 259.0/260.9 (bromine isotopes).

The synthetic route of 51760-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (274 pag.)WO2017/6295; (2017); A1;,
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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 653-92-9 as follows. Safety of Methyl 2-bromo-4-fluorobenzoate

To a solution of 5a (2.00 g, 8.58 mmol), Palladium acetate (0.008 g, 0.04 mmol), PPh3 (0.47 g, 1.69 mmol) and p-tolylboronic acid (10 mL) was added 6 mL of 2 M K2CO3. The mixture was refluxed under nitrogen for 5 h, then diluted with ethyl acetate, and washed with water (50 mL * 3) and brine (50 mL * 3).The organic layer was dried over MgSO4. The solvent was removed under reduced pressure.The residue was purified by flash column chromatography with petroleum ether-ethyl acetate (100/1) as eluant. The product was obtained as a yellow oil. Yield: 82.6%. 1H NMR (CDCl3, 400 MHz) delta: 7.53(1H, dd, J1 = 8.4 Hz, J2 = 2.8 Hz, Ph-H), 7.35(1H,dd, J1 = 8.4 Hz, J2 = 5.6 Hz, Ph-H), 7.25-7.16(5H, m, Ph-H), 3.69(3H, s, Ph-COOCH3)2.41(3H, s, Ph-CH3). ESI-MS (m/z): 245.2 [M+1]+.

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Da, Ya-Jing; Yuan, Wei-Dong; Xin, Ting; Nie, Yong-Yan; Ye, Ying; Yan, Yi-Jia; Liang, Li-Sha; Chen, Zhi-Long; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7101 – 7111;,
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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. 2905-65-9, name is Methyl 3-chlorobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-chlorobenzoate

Pd(OAc)2 or Pd2(dba)3/2-Catalyzed Amination of Aryl chlorides (Table 5).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 or Pd2(dba)3 (x mol %, see Table 5) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl chloride (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 5) was then added via syringe from a stock solution. Aryl chloride (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at 110 C. until the starting material had been completely consumed as judged by TLC (24 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

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; Iowa State University Research Foundation, Inc.; US7385058; (2008); B1;,
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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 107947-17-1 as follows. Recommanded Product: 107947-17-1

To a solution of commercially available methyl 3-bromo-4-chlorobenzoate (5.00 g, 20.0 mmol) dissolved in MeOH (100 ml.) at 20-25C was added Eta2NuNuEta220 (3.07 g, 61.3 mmol) and the mixture was heated at reflux temperature over night. After that time, the resulting mixture was concentrated under reduced pressure, the residue was suspended in MTBE, the solid contents collected via filtration and dried in a vacuum oven to afford the title compound (4.34 g, 87%). (0560) LC-MS: Mass calculated for C7H7BrCIN20+ [(M+H)+)] 248.9, found 248.9; RT = 0.756 min.

According to the analysis of related databases, 107947-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; GOCKEL, Birgit; HUWYLER, Nikolas; KOERBER, Karsten; NARINE, Arun; MCLAUGHLIN, Martin John; (82 pag.)WO2018/224455; (2018); A1;,
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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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3-chlorocyclobutanecarboxylate

Step 1: Preparation of 3-((3-(Methoxycarbonyl)cyclobutyl)thio)benzoic Acid, Intermediate 20.0 A mixture of 3-mercaptobenzoic acid (2.1 g, 13.5 mmol), methyl 3-chlorocyclobutanecarboxylate (4.0 g, 26.9 mmol; purchased as a 9:1 diastereomeric mixture (favoring trans) from Synthonix, Inc.), and potassium carbonate (7.43 g, 53.8 mmol) in DMF was stirred at 50 C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by MPLC using silica gel and eluting with a 0-40% EtOAc/EtOH (3:1) in heptane to provide 3-((3-(methoxycarbonyl)cyclobutyl)thio)benzoic acid (2.02 g) as white powder. 1H NMR (400 MHz, DMSO-d6) delta 12.91-13.22 (m, 1H), 7.74-7.77 (m, 2H), 7.44-7.49 (m, 2H), 3.96 (tt, J=7.77, 8.97 Hz, 1H), 3.56-3.61 (m, 3H), 3.11-3.23 (m, 1H), 2.67-2.73 (m, 2H), 2.10-2.21 (m, 2H). LCMS-ESI (POS.) m/z: 289.0 (M+Na)+.

The synthetic route of 15963-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39520-24-6, name is Dimethyl 2-isobutylmalonate, 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 39520-24-6, HPLC of Formula: C9H16O4

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.997 g, 24.9 mmol) in diethyl ether (100 mL) was added dimethyl 2- isobutylmalonate (3.13 g, 16.6 mmol) dropwise. The resulting mixture was stirred at RT for 3 h. The reaction mixture was cooled to 0 C. N-chloromethyl phthalimide (3.24 g, 16.6 mmol) was added in one portion. The reaction mixture was stirred at RT overnight followed by heating to reflux for 1 h. The reaction mixture was cooled to RT and cold 1.5 N HC1 (100 mL) was added. The organic layer was separated. The aqueous layer was extracted with diethyl ether (2 x 50 mL). The combined ether layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (5.3 g, 15.2 mmol, 92 % yield). The crude product was taken to next step without further purification. LCMS (ESI) m/e 347.9 [(M+H)+, calcd for Ci8H22N06, 348.1]; LC/MS retention time (method C): tR = 1.95 min.

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, Dimethyl 2-isobutylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, 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 175278-29-2, COA of Formula: C9H9FO2

Compound I-16B (15 g, 90 mmol) was added to a solution of concentrated sulfuric acid (200 mL).The ice bath was cooled to below 5 degrees Celsius and then NBS (17.8 g, 100 mmol) was added portionwise. The resulting mixture was stirred at 0 C for 3 hours, then at room temperature and stirred for 16 hours.Then slowly pour the mixture into ice water (2L).It was extracted with EtOAc (500 mL x 3).The combined organic layers were washed with water and brine.Drying and concentration gave Compound I-16C (22 g).

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 5-fluoro-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Dankang Pharmaceutical Biological Co., Ltd.; Xu Yong; Huang Lu; Lin Dang; Hu Hai; (31 pag.)CN110092745; (2019); A;,
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Synthetic Route of 18595-12-5,Some common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

To a 0 C. solution of methyl 5-amino-2-methylbenzoate (6.25 g, 37.8 mmol) in H2SO4 (10 mL) and H2O (160 mL) was added NaNO2 (aq., 3.78 N, 10 mL). The resulting mixture was stirred at 0 C. for 10 minutes. After 10 minutes, the mixture was added to a refluxing solution of CuSO4 (1 N, 100 mL) and refluxed for 1 hour. The mixture was cooled to room temperature and extracted with CH2Cl2 (2*200 mL). The organic layers were washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give methyl 5-hydroxy-2-methylbenzoate (134a, 4.2 g, 67%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-amino-2-methylbenzoate, its application will become more common.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
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Reference of 206551-41-9, 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. 206551-41-9 name is Methyl 3-bromo-2-fluorobenzoate, 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 1: Methyl 3-((2-chloro-5-(1 ,4-dimethyl- 1H-1 ,2,3-triazol-5-yl)pyridin-3- yl)amino)-2-fluorobenzoateTo a 70 mL pressure vial containing 2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5- yl)pyridin-3-amine (Step 1 of Example 54, 500 mg, 2.24 mmol), methyl 3-bromo-2-fluorobenzoate (Oakwood, 781 mg, 3.35 mmol) and Cs2CO3 (728 mg, 2.24 mmol) in dioxane (10 mL) was added 1,1 ?-bis(diphenylphosphino)ferrocene (62.0 mg, 0.11 mmol), Pd(OAc)2 (85 mg, 0.38 mmol) and Xantphos (65 mg, 0.11 mmol). N2 was bubbled through the reaction mixture for 2 mm. The vial was sealed and heated to 100 °C for 24h. BrettPhos precatalyst (100 mg, 0.12 mmol) and additional methyl 3-bromo-2-fluorobenzoate (781 mg, 3.35 mmol) were added. N2 was bubbled through the reactionmixture for 2 mm, and then heating was continued at 110 °C for 24 h. Additional BrettPhos precatalyst (100 mg, 012 mmol) was added and stirring was continued at 120°C for 5 h. BrettPhos precatalyst (100 mg, 0.12 mmol) was again added and the reaction mixture was heated at 120 °C for 5 h. After cooling to room temperature, the mixturewas diluted with CHC13 and filtered through Celite® rinsing with CHC13. The filtrate was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0percent to 100percent EtOAc/CH2C12) to give the title compound (140 mg, 17percent) as a white solid. ?H NMR (400 MHz, CDC13) oe 7.90 (d, J=2.1 Hz, 1H), 7.74 (ddd, J=8.0, 6.5, 1.7 Hz, 1H), 7.52 – 7.44 (m, 1H), 7.24 (d, J=0.9 Hz, 1H), 7.17 (t, J2.0 Hz, 1H), 6.34 (s, 1H),3.97 (d, J=0.7 Hz, 6H), 2.32 (s, 3H); LCMS (M+H) = 376.3; HPLC RT = 2.23 mm(Column: Chromolith ODS S5 4.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with0.1percent TFA; Mobile Phase B: 90:10 MeOH :water with 0.1percent TFA; Temperature: 40 °C;Gradient: 0-100percent B over 4 mm; Flow: 4 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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Reference of 711-01-3, 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 711-01-3 as follows.

Example-6; Charge Vitride (sodium dihydro-bis-methoxyethoxy alummate solution in toluene) reducing agent (200 gm) into a dry RBF at 25-35C under nitrogen atmosphere. Cool the Vitrideto 0C-5C. Slowly add toluene (300 ml) into RBF at 0C-5C. Prepare solution of XIII (100 gm) and toluene (200 ml) mixture; add this solution slowly to the reaction mass at 0C-5C. Maintain reaction mass for 10 min at 0C-5C. Raise the temperature to 25C-35C. Maintain the reaction mass for 1 hr at 25C-35C. Check TLC. After TLC complies, cool the reaction mass to 0C-5C. Slowly add saturated ammonium chloride solution to the reaction mass at 0C-5C. Maintain for 10-15 min. at 0C-5C. Filter the salts and wash with toluene (250 ml). Separate the organic layer and aqueous layer. Wash the toluene layer with sodium chloride solution (250ml x 2). Distill toluene out completely under vacuum at or below 70C. Residue weight: 95 gm. (Compound XIV).

According to the analysis of related databases, 711-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APICORE, LLC; KOVI, Ravishanker; RAPOLE, Keshavrao; NAIK, Ashish; KANNAPAN, Jayaraman; MADALA, Muralikrishna; THAKOR, Sanjay, F.; WO2012/162507; (2012); A1;,
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