Tag: M.W=200-300

Reference of 6624-71-1,Some common heterocyclic compound, 6624-71-1, name is Dodecyl isobutyrate, molecular formula is C16H32O2, 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 I Dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate STR7 To a solution of diisopropylamine (5.56 g, 0.055 mole) in 200 ml of dry ether at 0 C. under nitrogen is added with stirring n-butyllithium (0.055 mole) in hexane (31 ml). The resulting mixture is cooled to -70 C., and a solution of dodecyl isobutyrate (12.8 g, 0.05 mole) in ether (25 ml) is added dropwise over a period of 20 minutes. The mixture is warmed to -15 C., and a solution of 2,3-butanedione (4.73 g, 0.055 mole) in ether (10 ml) is added rapidly. The mixture then is stirred at -5 C. for 15 minutes. The reaction mixture is combined with 200 ml of saturated ammonium chloride solution, and the separated organic layer is washed in sequence with 200 ml of 0.5N HCl, 200 ml of saturated sodium bicarbonate, and 200 ml of saturated sodium chloride. The solution is dried over magnesium sulfate and the solvent is removed under reduced pressure to give 19 g of an oil. The oil is distilled in a Kugelrohr apparatus (air bath temperature 85-115 C. at 0.1 mm Hg) to provide 13.5 g of almost pure product. Fractional distillation of the oil yields 11.5 g of pure product (67%), b.p. 132-133 C. at 0.05 mm Hg. IR and NMR data confirm the above structure. Anal. calc. for C20 H38 O4: C, 70.13; H, 11.18. Found: C, 70.11; H, 11.24.

The synthetic route of 6624-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Philip Morris Incorporated; US4701282; (1987); A;,
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Adding a certain compound to certain chemical reactions, such as: 99548-55-7, name is Methyl 4-bromo-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 99548-55-7, COA of Formula: C9H9BrO2

General procedure: A mixture of methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

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

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
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Related Products of 57381-59-6, These common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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.

Compound 46b (24.00 g, 102.99 mmol) was dissolved in methanol (300 mL), and N,N-dimethylformamide (100 mL), triethylamine (100 mL), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (12.62g, 15.45 mmol) were added. The reaction mixture was stirred under a carbon monoxide atmosphere (50 psi) for 16 hr at 80 C, filtered, concentrated under reduced pressure, and extracted with ethyl acetate (500 mL×2). The organic phases were combined, dried, concentrated under reduced pressure to dryness, and purified by silica gel column chromatography (petroleum ether/ethyl acetate=100-0%), to give Compound 46c (11.00 g). 1H NMR (400 Hz, CDCl3) delta 3.95(s, 3H), 3.97(s, 3H), 7.20-7.24 (m, 1H), 8.21-8.23 (m, 1H), 8.63-8.65 (m, 1H). MS-ESI calculated value [M+ H]+ 213, measured value 213.

The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; YAO, Yuanshan; CHEN, Bin; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (102 pag.)EP3489233; (2019); A1;,
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17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, 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. SDS of cas: 17100-63-9

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 3.87 (s, 3H), 7.42 (dd, 1 H), 7.50 (d, 1 H), 7.68 (d, 1 H), 13.21 (br. s., 1 H).

The synthetic route of 17100-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; BRUENING, Michael; WO2013/87579; (2013); A1;,
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Related Products of 110661-91-1, 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. 110661-91-1, name is tert-Butyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 15 Synthetic Scheme A: Compounds 305, 298, 299, 300, 301, 302, and 303 tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)butanoate (1). To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (209.12 mg, 0.95 mmol) and tert-butyl 4-bromobutanoate (212 mg, 0.95 mmol) in N,N-Dimethylformamide (2 mL) was added Cs2CO3 (402.47 mg, 1.24 mmol). Reaction mixture was heated at 65 C. for 12 hours (overnight) . By TLC small amounts of starting material (Hex:AcOEt, 7:3). Crude product was purified by flash CC (SiO2-25 g, Hex:AcOEt, gradient 9:1 to 4:6) to give 198 mg (57% yield) of product as an oil: 1H NMR (500 MHz, DMSO-d6) delta 7.59 (d, J=8.2 Hz, 2H), 6.91 (d, J=7.9 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 2.35 (t, J=7.3 Hz, 2H), 1.92 (p, J=6.7 Hz, 2H), 1.39 (s, 9H), 1.27 (s, 12H). 13C NMR (101 MHz, dmso) delta 172.25, 161.56, 136.66, 114.37, 83.77, 80.12, 66.81, 31.72, 28.20, 25.12, 24.71. LC-MS (ESI); m/z [M+Na]+: Calcd. for C20H31BO5Na, 385.2162. Found 385.2194.

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

Reference:
Patent; Arvinas, Inc.; Yale University; Crew, Andrew P.; Hornberger, Keith R.; Wang, Jing; Dong, Hanqing; Qian, Yimin; Crews, Craig M.; Jaime-Figueroa, Saul; (628 pag.)US2018/179183; (2018); A1;,
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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, Recommanded Product: methyl 5-bromo-2-methyl-benzoate

5-Bromo-2-methylphenyl)methanolTo a solution of methyl 5-bromo-2-methylbenzoate (108 g, 471 mmol) in THF (1600 mL) was added LiAIH4(21.47 g, 566 mmol) slowly under nitrogen at 0 C. The resulting mixture was stirred at 0 C for 1 hr. Then 3.73 mL of water was added to the reaction mixture, followed by 3.75 mL of 10% NaOH, and 1 1.19 mL of water, filtered and concentrated to afford the title compound (5-bromo-2-methylphenyl)methanol (88 g, 416 mmol, 88 % yield). LC-MS MS m/z 185.1 (M-OH)+, 1.59 (ret. time)

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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 41841-16-1, Product Details of 41841-16-1

At 40 C., a solution of intermediate B.i (52 g) in THF (100 mL) was carefully added over a period of 40 min to a suspension of NaH (15.6 g) in dry THF (450 mL). Stirring was continued for 70 min without heating and the temperature dropped to 27 C. The evolution of gas stopped before dimethylcarbonate (76.42 mL) was added dropwise while the temperature of the mixture was maintained at 29-31 C. Stirring was continued for 22 h at rt. The mixture was cooled to -10 C. and then carefully neutralized to pH 6-7 with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in EA (700 mL), washed 3 times with 1 N aq. HCl-solution and once with brine, dried over MgSO4. Most of the EA was evaporated before Hex was added. The product crystallised overnight at 4 C. The crystals were collected, washed with Hex and dried to give the expected product as pale yellow crystals (45.9 g).1H-NMR (D6-DMSO): delta 3.66 (s, 6H); 5.07 (s, 1H); 7.30-7.34 (m, 2H); 7.55-7.59 (m, 2H),

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bolli, Martin; Boss, Christoph; Treiber, Alexander; US2012/142716; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate

A 500 ml one-necked flask was charged with ethyl 6-chloroimidazo [1,2-b] pyridazine-3-carboxylate (11.28 g, 50 mmol)And methanol 50ml,Sodium hydroxide (4.0 g, 100 mmol)Dissolved in 100ml of water,Added to the reaction flask,The reaction was completed at 25 C for 4 hours. The reaction was completed by TLC and neutralized with 30% hydrochloric acid until pH = 4. The mixture was suction filtered, the filter cake was washed with a small amount of water,Dry to give 6-chloroimidazo [1,2-b] pyridazine-3-carboxylic acid purity, yield 91%.

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; Shandong Youbang Biochemical Technology Co., Ltd.; Tan Pingzhong; Geng Xuanping; Cheng Wei; Lai Xinsheng; Lai Chao; Lai Ziteng; (7 pag.)CN106831782; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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 40876-98-0, Application In Synthesis of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

[4-((1R,5S,7S)-(1S,6R,8R)-9-bicyclo[4.3.1]dec-8-yl-3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-acetic acid ethyl ester (d6) To a solution of c1 (578 mg, 1.64 mmol) in ethanol (6 mL) was added oxalacetic acid diethyl ester sodium salt (977 mg, 4.41 mmol) and acetic acid (0.505 mL, 8.83 mmol) at temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at 100 C. for 8 hr. The reaction mixture was diluted with saturated aqueous NaHCO3, then extracted with CHCl3 (2*30 mL). The combined organic phases were washed with saturated aqueous NaCl and dried (MgSO4) and concentrated. The resulting brown solid was chromatographed (silica-gel 45 g, AcOEt/n-hexane=1/3?1/0) to provide 385 mg of compound d6 as a light brown solid. (Yield 49%) d6: 1H-NMR (300 MHz, CDCl3) delta: 1.23-1.38 (m, 2H), 1.28 (t, J=7.2 Hz, 3H), 1.42-1.88 (m, 12H), 2.08-2.32 (m, 4H), 2.35-2.60 (m, 2H), 3.14 (m, 1H), 3.33 (d, J=10.8 Hz, 2H), 3.64 (d, J=10.8 Hz, 2H), 3.74-3.84 (m, 2H), 3.94 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 5.94 (m, 1H), 7.30 (t, J=7.8 Hz, 1H), 7.53 (td, J=1.2 Hz, 7.8 Hz, 1H), 7.83 (dd, J=1.2 Hz, 7.8 Hz, 1H), 8.18 (brs, 1H); LC/MS: m/z=494.3[M+H]+ (Calc: 493).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
Ester – Wikipedia,
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Reference of 41841-16-1,Some common heterocyclic compound, 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 solution of methyl 2-(4-bromophenyl)acetate (1 g, 4.36 mmol) in dry THF (20 mL)was added LiHMDS (5.23 mL, 1 M) dropwise at -78 C under N2. The mixture was stirred at 0C for 2 h. After Mel (1.23 g, 8.72 mmol) was added at -78 C, the mixture was stirred at 20 Cfor 16 h. Quenched with NH4C1 sat. and extracted with EtOAc. The organic was concentratedand purified by silica gel colunm (PE/EtOAc = 1/0 to 100/1) to give the title product (642 mg,yield 6 1%). MS (ES+) C10H11BrO2 requires: 243, found 244 [M+H].

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-(4-bromophenyl)acetate, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BROOIJMANS, Natasja; BRUBAKER, Jason, D.; FLEMING, Paul, E.; HODOUS, Brian, L.; KIM, Joseph, L.; WAETZIG, Josh; WILLIAMS, Brett; WILSON, Douglas; WILSON, Kevin, J.; (347 pag.)WO2017/181117; (2017); A1;,
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