Tag: M.W=200-300

Related Products of 206551-41-9,Some common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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 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 min. The vial was sealed and heated to 100° C. for 24 h. 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 reaction mixture for 2 min, 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 mixture was diluted with CHCl3 and filtered through Celite® rinsing with CHCl3. The filtrate was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0percent to 100percent EtOAc/CH2Cl2) to give the title compound (140 mg, 17percent) as a white solid. 1H NMR (400 MHz, CDCl3) delta 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, J=2.0 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 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1percent TFA; Mobile Phase B: 90:10 MeOH:water with 0.1percent TFA; Temperature: 40° C.; Gradient: 0-100percent B over 4 min; Flow: 4 mL/min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromo-2-fluorobenzoate, its application will become more common.

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; (220 pag.)US2016/176864; (2016); A1;,
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Reference of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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.

6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-trifluoromethyl-pyridin-3-ylamine from example 5, step 4 (0.132g, 0.30mmol) was dissolved in dry acetonitrile (5ml) followed by the addition of 4-chlorosulfonyl-benzoic acid methyl ester (0.070g, 0.33mmol) and pyridine (0.071g, 0.90mmol). The reaction mixture was stirred for 12h at 50C, N-methylmorpholine (0.03g, 0.3mmol) was added and stirring was continued for 8h. The reaction mixture was concentrated under reduced pressure and purified by reversed phase HPLC (column Reprosil-Pur C18-A9, 250×20 mm, gradient elution acetonitrile:water (2:1) – pure acetonitrile) followed by column chromatography on silica (eluent hexanes:ethyl acetate 3:1) to give 0.060 g (31%) of 4-{6-[3-(2,6-dichlorophenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-trifluoromethyl-pyridin-3-ylsulfamoyl}-benzoic acid methyl ester as colourless oil.

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Phenex Pharmaceuticals AG; EP1894924; (2008); A1;,
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Synthetic Route of 30448-43-2, 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. 30448-43-2 name is Di-tert-butyl phthalate, 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.

General procedure: To a 500 ml four-necked flask equipped with a stirring, a thermometer, a distillation apparatus, and a constant pressure dropping funnel, 200 g of toluene and 17.0 g of potassium t-butoxide (0.15 mol) were added, and the mixture was heated to an internal temperature of 100-105 C. 27.8 g (0.1 mol) of di-tert-butyl phthalate and 20.0 g (0.12 mol) of a mixture of tert-butyl 3-cyanobutanoate were added dropwise, while t-butanol was distilled off, and the mixture was stirred at 100 C for 3 hours. . Cool to 20-25 C, add 20 grams of 20% aqueous sodium hydroxide solution, stir the reaction at 20-30 C for 3 hours; connect the tail gas absorption device with lye, then add 30% hydrochloric acid to the reaction bottle to adjust the pH value The reaction was stirred at 2.0-2.5, 60 C for 3 hours; the layers were separated, and the aqueous layer was extracted with toluene three times, 50 g each time. The organic phases were combined, and toluene was distilled away to give 15.8 g of 2-methyl-1,4-naphthoquinone in a yield of 91.9%. The purity of GC was 99.7%.

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

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Qu Hu; Ju Lizhu; (6 pag.)CN109384659; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, 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 79669-50-4, Product Details of 79669-50-4

90. To a solution of methyl 5-bromo-2-methylbenzoate (1.5g, 6.548 mmol) in CCL (35 mL) was added NBS (1.4g, 7.86 mmol) followed by AIBN (65 mg, 0.393 mmol). The reaction mixture was heated at reflux for 6h. After reaction finished, the reaction mixture was poured into water and extracted with dichloromethane (50 mL x 3). The combined organic layers were dried with Na2SO4, filtered, concentrated. The residue was purified by chromatography (silica gel, hexane/EtOAc = 1 00/0 – 20/80) to give methyl 5-bromo-2- (bromomethyl)benzoate (1.513g, 75%).

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-bromo-2-methyl-benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GERO DISCOVERY LIMITED LIABILITY COMPANY; FEDICHEV, Petr Olegovich; GREENMAN, Kevin; CHIH-TSUNG, Chang; KHOLIN, Maksim Nikolaevich; GETMANTSEV, Evgeny Gennadievich; ZHIDKOVA, Tatiana Vladimirovna; KADUSHKIN, Alexandr Viktorovich; PYRKOV, Timofei Vladimirovich; SHISHOV, Dmitry Veniaminovich; BOLANOS-HERNANDEZ, Juan Pedro; ZAKURDAEVA, Kristina Aleksandrovna; BURMISTROVA, Olga Andreevna; (573 pag.)WO2020/80979; (2020); A1;,
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Related Products of 40876-98-0, These common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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.

Step 1: 6-Hydroxypyrimidine-4-carboxylic acid 63.5 g (0.3 mol) sodium diethyloxalacetate and 30.2 g (0.3 mol) formamidine acetate were added to 24.1 g (0.6 mol) NaOH in 3.6 L water. The mixture was stirred overnight at RT. Then activated charcoal was added and the mixture was refluxed for 1 h. It was filtered off while hot and after cooling acidified with a hydrochloric acid solution. The solution was concentrated to dryness by rotary evaporation. The residue contained the desired product and was used in the next step without any further purification. Yield: 83.0 g

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
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Some common heterocyclic compound, 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, molecular formula is C9H16ClNO2, 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. COA of Formula: C9H16ClNO2

Step 1. Preparation of methyl 8-(1-(2-chloro-6-(trifluoromethyl)benzoyl)- 1H- pyrazolo [4,3-bj pyridin-3-yl)-8-aza-bicyclo [3.2.11 octane-3-carboxylate (B-2).A mixture of (3 -bromo- 1 H-pyrazolo [4,3 -b]pyridin- 1 -yl)(2-chloro-6-(trifluoromethyl)phenyl)methanone (B-i) (200mg, 0.5 Ommol), 3 -(methoxycarbonyl)-8-azonia-bicyclo[3.2.1]octane chloride 2 (0.15 g, 0.75 mmol) and Cs2CO3 (0.65g, 2.Ommol) were suspended in DMF (5mL). The reaction mixture was heated at 150C in a microwave reactor for 5h. The resulting mixture was diluted with H20 (5OmL). 2M HC1 solution was added to adjust the pH to 3 and the aqueous layer was extracted with ethyl acetate (3x2OmL). Thecombined organic layers were washed with brine (2OmL), dried over anhydrous Na2SO4 and concentrated to obtain the crude product B-2 as yellow oil. LCMS (ESI) calc?d for C23H20C1F3N403 [M+H]: 493, found: 493

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 179022-43-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
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Synthetic Route of 107317-58-8, 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. 107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of the product from Step A (17.3 g, 61.2 mmol) in 1,4-dioxane is added A- (4,4,5, 5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-buty ester (18.9 g, 61.2 mmol), 2 M aqueous potassium carbonate (61.2 mL, 122 mmol), and tetrakistriphenylphosphinepalladium(O) (7.07g, 6.10 mmol). The reaction vessel is sealed and heated to 140 C for 4 hours. The mixture is cooled to room temperature and the dioxane is removed in vacuo. The resulting residue is diluted with water and ethyl acetate, filtered to remove insoluble material, and the layers are separated. The aqueous layer is extracted twice with ethyl acetate and the combined organics are dried over Na2SO4, filtered, and the solvent is removed in vacuo. The brown residue is then passed through a short bed of silica rinsing first with 10% ethyl acetate in hexane, then 20% ethyl acetate in hexane. The material collected from the 20% ethyl acetate fraction is evaporated to afford the desired product as a light yellow solid (19.6 g, 83%). LCMS: 371.51 (M+CEta3CN-56).

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-bromo-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; BENTZIEN, Joerg, Martin; BOYER, Stephen, James; BURKE, Jennifer; ELDRUP, Anne, Bettina; GUO, Xin; HUBER, John, David; KIRRANE, Thomas, Martin; SOLEYMANZADEH, Fariba; SWINAMER, Alan, David; WO2010/5783; (2010); A1;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

The intermediate N-(l-methyl-6,7-dihydrocyclohepta[fJindol-5(lH)-ylidene)prop-2-en- 1 -amine obtained above (ca. 8.46 mmol) and trimethyl methanetricarboxylate (2.75 g, 14.46 mmol) were mixed together in PI12O (17 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes, followed by EtOAc/hexanes 0-80% gradient) to provide the product as a yellow solid (2.15 g, 56% overall). ^ MR ^OO MHz, CHCl3-i/) 8 ppm 2.1 1 (ddd, J=14.1, 5.8, 2.0 Hz, 1 H) 3.51 (dd, J=14.1, 8.0 Hz, 1 H) 3.86 (s, 3 H) 4.01 (s, 3 H) 4.38 (dd, J=15.1, 5.9 Hz, 1 H) 4.53 (ddt, J=15.1, 4.6, 2.1 Hz, 1 H) 4.75 (dd, J=17.2, 1.1 Hz, 1 H) 5.05 (dd, J=10.4, 1.1 Hz, 1 H) 5.90 (dddd, J=17.2, 10.4, 5.9, 4.6 Hz, 1 H) 6.37 (ddd, J=9.8, 8.0, 5.8 Hz, 1 H) 6.53 (dd, J=3.2, 0.9 Hz, 1 H) 6.76 (dd, J=9.8, 2.0 Hz, 1 H) 7.20 (d, J=3.2 Hz, 1 H) 7.29 (s, 1 H) 7.85 (s, 1 H) 13.72 (br. s., 1 H). LC-MS 375.3 [M+H]+, 377.3 [M+H]+, RT 1.40 min.

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 1186-73-8.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Reference of 7686-78-4,Some common heterocyclic compound, 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, molecular formula is C11H16O4, 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.

The preparation method is:In an air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.4mmol of ethylene cyclopropane compound,0.003mmol of [Ru (p-cymene) Cl2] 2,0.04mmol are trimethylbenzoic acid,0.02mmol of silver hexafluoroantimonate, microwave reaction at 25 C for 2 hours;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0),Dried to a pale yellow oil,Yield: 70%, E / Z = 20: 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); 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. 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2967-66-0

General procedure: Pathway A-Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester previously isolated (0.01 mol) was added and the mixture was refluxed during 10 min. The cooling down was proceeded sequentially in a water bath, followed by ice bath and dry ice – ethanol bath. The solid was filtered and washed with cold water. Different conditions were needed to obtain 4-nitro-3-(trifluoromethyl)benzhydrazide (3d) and 4-nitrobenzhydrazide (3 h). Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was cooled down in ice bath to -3 to 2 C. The respective methyl ester (0.01 mol) was added and the mixture was stirred during 1 hour. The cooling down was proceeded in dry ice – ethanol bath. The solid was filtered and washed with cold water. Pathway B-each substituted benzoic acid (0.01 mol) was refluxed during 4 h in 20.0 mL (0.50 mol) of anhydrous methanol and 0.5 mL (1.0 mmol) of sulfuric acid. The reaction mixture was cooled down to room temperature. and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.11 mol) was added. The system was maintained into vigorously stirring for more 30 minutes. In the case of compounds with 4-nitro and 4-nitro-3-trifluoromethyl substituent groups attached in the benzene moiety, after the addition of hydrazine hydrate 80% (v/v) at room temperature, the reaction mixture was cooled down in ice bath and maintained into stirring during 1 hour. After these periods, the mixture was maintained at cold temperature to give 3.

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 2967-66-0.

Reference:
Article; Jorge, Salomao Doria; Palace-Berl, Fanny; Masunari, Andrea; Cechinel, Cleber Andre; Ishii, Marina; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 5031 – 5038;,
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