Tag: M.W=100-200

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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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 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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Application of 25081-39-4, 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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2 Preparation of methyl-3,5-bis(bromomethyl)-benzoate: A solution of methyl-3,5-dimethyl-benzoate (16.8 g, 0.10 mol) in carbon tetrachloride (150 ml) was treated with N-bromosuccinimide (35.6 g, 0.20 mmol), and benzoyl peroxide (500 mg, cat. amount), and heated to reflux. After 3 hours, the mixture was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was concentrated under reduced pressure and recrystallized from diethyl ether/hexanes (1:1) to yield the product (18.0 g, 55% yield) as a granular white solid. mp 64-70 C. (lit. mp 65-69 C.); TLC (20% ethyl acetate/hexanes): Rf =0.65 (UV active, CAM stain)

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 3,5-dimethylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Trustees of Columbia University in the City of New York; US5599926; (1997); A;,
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Electric Literature of 57486-68-7,Some common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, molecular formula is C9H9ClO2, 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 31 1-(o-Chlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride A stirred mixture of 36.9 g. of methyl o-chlorophenylacetate, 36.0 g. of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml. of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl alpha-bromo-o-chlorophenylacetate as a straw-colored liquid.

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

Reference:
Patent; American Cyanamid Company; US4435419; (1984); A;,
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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. 105-53-3, name is Diethyl malonate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Diethyl malonate

Reference Example 196 Ethyl 4-hydroxy-6-methylpyrimidine-5-carboxylate A mixture of diethyl malonate (4.8 mL), triethyl orthoacetate (17 mL), acetic anhydride (0.11 mL) and zinc chloride (1.2 g) was stirred at 140C. To the mixture was added acetic anhydride (0.11 mL) each after 30, 90 and 120 minutes, and then stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1 – 7/3) to give diethyl 2-(1-ethoxyethylidene)malonate (5.02 g). To a solution of diethyl 2-(1-ethoxyethylidene)malonate (4.13 g) in ethanol (15 mL) were added formamidine hydrochloride (1.73 g) and a solution of potassium hydroxide (2.21 g) in water (7.5 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized by adding acetic acid. To the mixture was added ethyl acetate (30 mL), and the mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate – ethyl acetate/methanol = 9/1) to give the title compound (1.5 g).

According to the analysis of related databases, 105-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); 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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., Product Details of 5335-05-7

Preparation of iodomethyl benzoate (6) Compound 6 was prepared by a modification of a literature procedure (Maury et al , Org. Lett. 2010, 12, 3590). Chloromethyl benzoate (2.7 g, 15.9 mmol) was dissolved in acetone (20 mL). Sodium iodide (7.1 g, 47.6 mmol) was added, and the resulting mixture was stirred for 3 hours at 45 C, diluted with acetone (100 mL), filtered in the absence of light, and evaporated under reduced pressure at < 30 C. The residue was dissolved in diethyl ether (100 mL), washed with aqueous sodium bicarbonate and aqueous sodium thiosulfate, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure at < 30 C in the absence of light, yielding compound 6 as a yellow oil (3.3 g, 79%). The analytical data for compound 6 were identical to those reported in Maury el al , Org. Lett. 2010, 12, 3590. Compound 6 was used immediately in the subsequent step. 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; KALA PHARMACEUTICALS, INC.; ONG, Winston Zapanta; NOWAK, Pawel Wojciech; KIM, Jinsoo; ENLOW, Elizabeth M.; BOURASSA, James; CU, Yen; POPOV, Alexey; CHEN, Hongming; WO2014/144285; (2014); A1;,
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