Tag: M.W=200-300

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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., Product Details of 29263-94-3

A mixture of diethyl 2-bromo-2-methylmalonate (1 equiv.), malononitrile (1 equiv.) and potassium t-butoxide (1 equiv.) in THF was heated to reflux for 15 h. The mixture was diluted with ethyl acetate and saturated aqueous ammonium chloride solution and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give an oil. The oil was purified by silica gel chromatography (10-15%) ethyl acetate in hexane gradient) to give diethyl 2-(dicyanomethyl)-2-methylmalonate (5.76 g, 32 %> yield) as a colorless oil. 1H NMR (500 MHz, CDC13) delta ppm 4.53 (s, 1 H), 4.27 – 4.39 (m, 4 H), 1.81 (s, 3 H), 1.33 (t, 6 H).

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (2016); 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 2-(4-bromophenyl)acetate

Example 13A Ethyl 2-(4-bromophenyl)-2-methylpropanoate 2.0 g (8.2 mmol) of ethyl (4-bromophenyl)acetate were dissolved in 50 ml of DMF, and 0.7 g (18 mmol) of sodium hydride in mineral oil (60%) were added at RT. The mixture was stirred at RT for 30 minutes, after which 2.9 g (20.6 mmol) of iodomethane were added. The mixture was then stirred at RT overnight. The mixture was diluted with ethyl acetate and extracted first with water and then with saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 mum, 250 mm*40 mm (30% methanol/70% water to 100% methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.75 g (78% of theory) of an oil. GC-MS [Method 5]: Rt=5.10 min; MS(ESIpos): m/z=270/272 (M+) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.11 (t, 3H), 1.48 (s, 6H), 4.06 (q, 2H), 7.24-7.29 (m, 2H), 7.50-7.54 (m, 2H)

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 14062-25-0.

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;,
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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 91-44-1 as follows. Formula: C14H17NO2

To a 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 155 muL (0.90 mmol) of compound E-2 and stirring for 24 hours under blue light irradiation, compound H-4 was obtained with a yield of 82%.

According to the analysis of related databases, 91-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
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Synthetic Route of 21597-54-6, 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. 21597-54-6, name is Methyl 3-amino-2-naphthoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of Intermediate (C) (0258) 15 g (74.5 mmol) of Intermediate (B) was added to 200 mL of tetrahydrofuran (THF). Then, while slowly stirring the resulting mixture, 5.72 g (149 mmol) of NaH (60% dispersion in mineral oil) was added dropwise thereto. The obtained reaction mixture was refluxed at a temperature of about 60 C. for about 72 hours, cooled to room temperature, and 250 mL of distilled water was added thereto to complete the reaction. 500 mL of 2N HCl was slowly added to the resulting reaction mixture, followed by stirred for about 60 minutes. The formed solid product was subjected to filtration and washed using distilled water. The formed solid product was vacuum-dried, thereby obtaining 8.07 g of Intermediate (C) (yield: 64%). 1H NMR (300 MHz, DMSO-d6): 10.5 (s, 2H), 7.92 (m, 4H), 7.88 (m, 4H), 7.64 (s, 2H), 7.46 (s, 2H).

The synthetic route of Methyl 3-amino-2-naphthoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY; Kim, Mikyung; Kim, Yunhi; Kwon, Soonki; Kim, Heeyeon; Park, Yunjee; Jeong, Hyein; Hwang, Jaeyoung; (77 pag.)US2017/77422; (2017); A1;,
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Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-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. Quality Control of Methyl 4-bromo-3-fluorobenzoate

To a solution of 8 (1.5g, 7.69mmol) in 1,4-dioxane was added 2eq. l-methyl-3- trifluoromethylpyrazole-5-boronic acid, Pd(dppf)2C12 (0.5g) and 3eq.K3P04. 3H20. The reaction mixture was sparged with nitrogen for 10 minutes. And the resulting mixture was stirred at 85C for 15 hours under the N2. EA/brine work and followed by prep HPLC purification to give 1.3 g compound 9. l .lg of 10 was obtained after hydrolysis with aq. LiOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 849758-12-9, its application will become more common.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
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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 17100-63-9 as follows. Safety of Methyl 4-bromo-3-methoxybenzoate

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (5.3 g) in THF (250 mL) was added methyl magnesium bromide (21.5 mL; c = 3.0 M) at room temperature and the mixture was heated to reflux for 1 h. A half-saturatedaqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chLoride soLution, dried (sodium suLfate) and the soLvent was removed in vacuum. Silicagel chromatography gave 3.09 g of the title compound.

According to the analysis of related databases, 17100-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; SCHIROK, Hartmut; KOSEMUND, Dirk; BRIEM, Hans; BADER, Benjamin; BOeMER, Ulf; WENGNER, Antje Margret; SIEMEISTER, Gerhard; LIENAU, Philip; STOeCKIGT, Detlef; LUeCKING, Ulrich; SCHALL, Andreas; WO2014/198594; (2014); 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. 15848-22-3, name is 5-Bromopentyl acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 15848-22-3

a 5-(3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)pentyl Acetate A solution of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol (10 g, 0.35 mol), 5-bromopentyl acetate (8.15 g) and potassium carbonate (33.6 g) in methyl ethyl ketone (200 ml) is refluxed for 2 hours. The reaction medium is treated with water and ethyl acetate. After separation of the phases by settling, the organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40 C. The product is purified by flash chromatography on a column of silica. Yellow oil. Yield: 93%.

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 15848-22-3.

Reference:
Patent; Galderma Research & Development S.N.C.; US6444709; (2002); B1;,
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These common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, 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. Recommanded Product: Methyl 6-bromohexanoate

Step-II: Preparation of methyl 6-(3-(benzo[d]oxazol-2-yl)-4-oxoquinolin-l(4H)- yl)hexanoate; To a mixture of 3-(benzo[d]oxazol-2-yl)quinolin-4(lH)-one (0.05 g, 1.9 mmol) and anhydrous K2CO3 (0.078 g, 5.7 mmol) in DMF (5 mL), methyl 6-bromohexanoate(0.079g, 3.8 mmol) was added and heated under microwave at 125 0C for 20 minutes. The reaction mixture was poured into ice-cold water (10 mL) and extracted with ethyl acetate (25 mL). The organic layer was washed with water, brine solution each 10 mL.The organic layer was dried over Na2SO4 and concentrated to afford the crude compound, was purified by column chromatography using 20percent ethyl acetate in hexane as an eluent. The pure fraction was concentrated to afford the title compound as colourless solid (0.055 g, 74.32 percent yield).

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

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD.; BALASUBRAMANIAN, Gopalan; RAJAGOPAL, Sridharan; RATHINASAMY, Suresh; KILAMBI, Narasimhan; RAJENDRAN, Praveen; NARAYANAN, Shridhar; WO2010/73078; (2010); A2;,
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Electric Literature of 706791-83-5,Some common heterocyclic compound, 706791-83-5, name is Methyl 3-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

TEA (0.909 ml_, 6.52 mmol) was added to a mixture of propionic acid (0.21 1 ml_, 2.83 mmol) and HATU (1 .157 g, 3.04 mmol) in DMF (1 .0 ml_). After 20 min, methyl 3-amino-5- bromobenzoate (CAS 706791 -83-5) (0.5 g, 2.173 mmol) was added and the resulting mixture was stirred at room temperature for 18 h. The reaction was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (heptane/EtOAc = 100:0 to 0: 100) to give the title compound. 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 8.20 (s, 1 H), 7.91 (app. d, J=2.0 Hz, 2 H), 7.15 (br. s. , 1 H), 3.93 (s, 3 H), 2.42 (q, J=7.5 Hz, 2 H), 1 .27 (t, J=7.6 Hz, 3 H).

The synthetic route of 706791-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Related Products of 1014645-87-4, 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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The title compound (D171) (58 mg) was prepared according to the experimental procedure described in Description 169 (reaction time 2 h) starting from 5-chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinic acid (D120) (55 mg, 0.157 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (D7) (35.8 mg, 0.157 mmol).

The synthetic route of Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
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