Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Computed Properties of C7H13BrO2

To the mixture of the A-4 (1500 mg, 5.08 mmol) and K2C03 (1402.39 mg, 10.16 mmol) in MeCN (5 mL) was added tert-butyl 3-bromopropanoate (1062.36 mg, 5.08 mmol), and the mixture was stirred at 50 C for 16 hours. The mixture was cooled to r.t, diluted with sat.NH4Cl (50 mL), extracted with EtOAc (50 mL x 2), and the combined phase was washed over brine (20 mL), dried over Na2S04 and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 5% to 10% to 20%) to afford A-24 (1300 mg, 3.07 mmol) as an oil. 1H NMR (DMSO-d6 400MHz) deltaH = 7.83 (d, 2H), 7.72 (s, 1H), 7.47 (d, 2H), 7.43 (s, 2H), 4.10 (t, 2H), 2.75 (t, 2H), 1.31 (s, 9H).

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-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-amino-4,5-dimethoxybenzoate

Step 1a. 6,7-Dimethoxyquinazolin-4(3H)-one (Compound 0102) A mixture of methyl 2-amino-4,5-dimethoxybenzoic acid 0101 (2.1 g, 10 mmol), ammonium formate (0.63 g, 10 mmol) and formamide (7 ml) was stirred and heated to 190~200 C. for 2 hours. Then the mixture was cooled to room temperature. The precipitate was isolated, washed with water and dried to provide the title compound 0102 as a brown solid (1.8 g, 84.7%): LCMS: m/z 207 [M+1]+; 1H-NMR (DMSO.) delta 3.87 (s, 3H), 3.89 (s, 3H), 7.12 (s, 1H), 7.43 (s, 1H), 7.97 (s, 1H), 12.08 (bs, 1H).

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2009/76022; (2009); A1;,
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Application of 20921-00-0, 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 20921-00-0 as follows.

To a mixture of compound 6B (3.41 g, 14.956mmol) in THF at 0 was added CH3MgBr (32.9 mmol) . The mixture was allowed to stir at 020 for 16 hours, and then the mixture was quenched with NH4Cl, and extracted with ethyl acetate. The organic extract was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. Tthe residue obtained was purified using flash column chromatography (petroleum ether: ethyl acetate 20: 15: 1) to provide compound 6C.

According to the analysis of related databases, 20921-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YU, Wensheng; KOZLOWSKI, Joseph A.; TONG, Ling; COBURN, Craig A.; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; (101 pag.)WO2018/32467; (2018); A1;,
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Electric Literature of 651734-58-6, These common heterocyclic compound, 651734-58-6, name is Methyl 2-fluoro-3,5-dimethoxybenzoate, 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.

Solution of 2-fluoro-3,5-dimethoxy-benzoic acid methyl ester (8.3 g, 38.7 mmol) in 330 mL of acetonitrile is cooled to O0C. Under nitrogen atmosphere SO2Cl2 (5.2 g, 38.7 mmol) is added dropwise. The reaction mixture is warmed to room temperature slowly. After 1 hour, the reaction is completed. The reaction is quenched with saturated sodium bicarbonate, and extracted with EtOAc three times. The organic layer is washed with brine, dried with MgSO4 and concentrated. The crude mixture is separated by silica gel column chromatography eluting with a gradient of hexane/ether (20:1 to 10:1 and 5:1) to obtain 2- chloro-6-fluoro-3,5-dimethoxy-benzoic acid methyl ester (20); 1H NMR 400 MHz(CDCl3) delta 6.64 (d, IH), 3.97 (s, 3H), 3.91 (s, 3H), 3.89 (s, 3H);MS m/z 249.0 (M + 1).

The synthetic route of 651734-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/8747; (2008); 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. 28170-07-2, name is Benzyl phenyl carbonate, A new synthetic method of this compound is introduced below., Safety of Benzyl phenyl carbonate

According to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195-2202.Benzyl phenylcarbonate (25,1 g, 1 10 mmol) was added dropwise to a solution of diethyl- enetriamine (5,16 g, 50 mmol) in dichloromethane (100 ml). The mixture was stirred for at least 20 h. The organic phase was washed with phosphate buffer (0.025 M K2HPO4, 0.025 MNaH2PO4, 2000 ml, pH adjusted to 3 with 2 M sulfuric acid). The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo.Yield: 25.2 g A portion (5 g) of the crude oil was mixed with hydrochloric acid (2 M, 15 ml). The mixture was stirred for 15 minutes. The mixture was filtered. The isolated solid was mixed with abs. ethanol (600 ml). The mixture was brought to reflux. The boiling mixture was decanted in order to remove insoluble impurities. The compound crystallized over night at 5 C.Yield: 2.84 g (white crystals) 1H-NMR (af-DMSO) delta: 8.96 (b, 2H), 7.51 (t, J = 5.56 Hz, 2H), 7.40-7.30 (b, 10H), 5,04 (s,4H), 3.33 (q, J = 6.06 Hz, 4H), 3.00 (b, 4H)13C- NMR (af-DMSO) delta: 156.6, 137.2, 128.7, 128.3, 128.2, 66.0, 46.8, 37.1LC-MS (ES-positive mode), m/z: 372.5 [M+H]+

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; NOVO NORDISK A/S; WO2006/79641; (2006); A2;,
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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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, A new synthetic method of this compound is introduced below., Computed Properties of C10H9BrO4

Dimethyl-5-bromoisophthalate (3 g, 11.0 mmol) was dissolved in acetone-H2O (2:1 v/v, 60 mL) and NaOH (0.40 g, 11.0 mmol) was added. The reaction mixture was allowed to stir for 4 h. Acetone was removed under reduced pressure and the aqueous layer was washed with EtOAc, acidified to pH ? 2-3 using 1.5N HCl, and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 3-bromo-5-(methoxycarbonyl)benzoic acid (2.55 g, yield 89%): 1H NMR (300 MHz, DMSO-d6) delta 13.75 (br s, 1 H), 8.40 (d, J = 1.0 Hz, 1 H), 8.26 (d, J = 1.4 Hz, 1 H), 8.23 (d, J = 1.0 Hz, 1 H), 3.89 (s, 3H). MS (ESI) m/z: Calculated for C9H7BrO4: 257.95; found: 258.0 (M+H)+.

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; Tempero Pharmaceuticals, Inc.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby; EP2533783; (2015); B1;,
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Application of 55666-42-7, The chemical industry reduces the impact on the environment during synthesis 55666-42-7, name is tert-Butyl 2-bromobenzoate, I believe this compound will play a more active role in future production and life.

Step 2 tert-butyl 4′-fluoro-3′-methyl-[1,1′-biphenyl]-2-carboxylate Tert-butyl 2-bromobenzoate (33.38 g, 129.8 mmol), (4-fluoro-3-methylphenyl)boronic acid (10 g, 64.9 mmol), Pd(PPh3)4(749 mg, 0.64 mmol), and Na2CO3 (13.7 g, 129.8 mmol) were dissolved in IPA (50 ml) and H2O (50 ml) in a 1 L flask, followed by reflux-stirring for 12 hours. The reaction mixture was concentrated under reduced pressure. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO4 and filtered. The mixture was separated by column chromatography to give tert-butyl 4′-fluoro-3′-methyl-[1,1′-biphenyl]-2-carboxylate (13 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, tert-Butyl 2-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hyundai Pharm Co., Ltd.; LEE, In Hee; CHAE, Hee Il; KIM, Se hoan; MOON, Soon Young; HA, Tae Young; CHOI, Hyo sun; KIM, Young Seok; KIM, Chun hwa; RHEE, Jae Keol; (132 pag.)US2016/355483; (2016); 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. 2557-13-3, name is Methyl 3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-(trifluoromethyl)benzoate

3-trifluoromethyl-benzoic acid methyl ester fluoride to 4.30g (21.1mmol)Cesium 92.6mg the (0.696mmol) added under an argon atmosphere, then cooled to -10 or less of. This trifluoromethyl trimethylsilane about 4mL (about 27mmol) was added dropwise at -10 or less. 1 hour at -10 C., further stirred for 1 hour at room temperature. Then extracted by the addition of methylene chloride and water to the reaction solution. The organic phase is dried over magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (developing solvent = n-hexane / ethyl acetate = 98/2 [volume]). Concentration collect a portion corresponding to Rf value of about 0.9, as a colorless transparent liquid trimethyl (2,2,2-trifluoro-1-methoxy-1- (3- (trifluoromethyl) phenyl) ethoxy) silane 4.46g (65%) obtained. Incidentally, Rf is selected from the group consisting of the ratio of distance traveled from the origin with respect to the distance from the origin to the solvent front of the sample of interest (relative moving distance).

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; NIPPON SODA COMAPNY LIMITED; ITO, YOSHIKAZ; KUBOTA, YASUSHI; ICHINARI, DAISUKE; INOUE, HIROKI; IWATA, JYUN; NAKASHIMA, RYOYO; KURUSHIMA, HIROAKI; MATSUDA, KEIICHIRO; KUTOSE, KOICHI; (90 pag.)JP5653442; (2015); B2;,
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These common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, 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. Product Details of 106896-49-5

A flame-dried flask, equipped with a reflux condensor, containing methyl 4- amino-3-bromobenzoate (2.5 g, 10.87 mmol), bis(neopentyl glycolato)diboron (3.07 g, 13.58 mmol), potassium acetate (3.20 g, 32.6 mmol), and PdC^dppf -CH^C^ adduct(0.222 g, 0.272 mmol) was added degassed DMSO (31.0 mL). The resulting dark red- brown suspension was warmed to 85 C. After 2.5 h, the resulting dark black reaction was cooled to RT and poured into cold water (100 mL) to give a suspension. The suspension was extracted with EtOAc (3x). The combined organic layers were washed with sat. aHC03, brine, dried over sodium sulfate, filtered and concentrated to give a brown solid weighing 3.1 g. Purification by normal phase chromatography gave 1.64 g (55%) of Intermediate 39 as a pale, yellow solid. lH NMR (500 MHz, CDC13) delta ppm8.35 (d, J=2.20 Hz, 1 H), 7.84 (dd, J=8.53, 2.20 Hz, 1 H), 6.52 (d, J=8.53 Hz, 1 H), 5.25 (br. s., 2 H), 3.84 (s, 3 H), 3.79 (s, 4 H), 1.03 (s, 6 H). MS (ESI) m/z: 196.0 (M-C5H8+H)+

The synthetic route of Methyl 4-amino-3-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James, R.; FANG, Tianan; DECICCO, Carl, P.; PINTO, Donald, J., P.; ROSSI, Karen, A.; HU, Zilun; JEON, Yoon; QUAN, Mimi, L.; SMALLHEER, Joanne, M.; WANG, Yufeng; YANG, Wu; WO2011/100401; (2011); A1;,
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Electric Literature of 61500-87-6, 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. 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-4-trifluoromethyl-benzoic acid methyl ester, (48 g, 219 mmol) was dissolved in MeOH (750 ml). Silver sulfate (68.3 g, 219 mmol) and iodine (55.6 g, 219 mmol) was added and rinsed in with MeOH (50 ml). The reaction mixture was left for 1 hour at RT. The reaction mixture was filtered under vacuum and the filtrate concentrated in vacuo. The residue was taken up in MeOH (100 ml) and water (10 ml) and the mixture heated at 80C. The crude solution was hot filtered to remove residual inorganics and the warm filtrate was poured slowly into water (750 ml) with vigorous stirring. The mixture was left to particulate for 10 minutes and filtered to give the title compound as an orange solid. MS m/z 345[M+H]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
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