Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 5164-76-1, name is Dimethyl pent-2-enedioate, 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 5164-76-1, COA of Formula: C7H10O4

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

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:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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Adding a certain compound to certain chemical reactions, such as: 927-68-4, name is 2-Bromoethyl 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 927-68-4, Recommanded Product: 2-Bromoethyl acetate

(R)-7-chloro-N-(piperidin-3 -yl)-4-(trifluoromethyl)benzo[b]thiophene-2-carboxamide (TFA salt, 95 mg, 0.20 mmol), Nal (50 mg, 0.33 mmol), K2C03 (180 mg, 1.30 mmole), 2- bromoethyl acetate (32 uL, 0.29 mmol) and DMF (2 mL) were added into a reaction flask, and stirred at room temperature overnight. The mixture was dissolved in ethyl acetate (20 mL) and water (5 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2x). The ethyl acetate layer was concentrated in vacuo and chromatographed on silica gel using hexanes and ethyl acetate to give title compound (50 mg, 0.11 mmol, 56%). ?H NMR (CD3OD, 400 MHz) 8.34 (s, 1H), 7.83 (dd, IN, J 0.4, 8.0 Hz), 7.68 (dd, 1H, J?0.4, 8.0 Hz), 4.50 (m, 2H), 4.38 (m, 1H), 3.73 (m, 1H), 3.56 (m, IH), 3.32 (m, 2H),3.02 (m, 2H), 2.14 (m, 5H), 2.00 (m, 2H), 1.79 (m, 2H). LCMS (ES) 449, 451 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoethyl acetate, and friends who are interested can also refer to it.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; ICAHN SCHOOL OF MEDICINE AT MONT SINAI; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; KAMENECKA, Theodore, M.; KENNY, Paul; LINDSTROM, Jon, M.; WANG, Jingyi; JIN, Zhuang; DOEBELIN, Christelle; (95 pag.)WO2016/191366; (2016); A1;,
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Electric Literature of 22223-49-0, The chemical industry reduces the impact on the environment during synthesis 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, I believe this compound will play a more active role in future production and life.

Example 64 – Preparation of methyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate Methyl 3-methylanthranilate (2.1 g, 13 mmol) was dissolved in 4 ml pyridine and 6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After a mild exothermic reaction subsided the reaction mixture was stirred at 50C for 24 hours. The pyridine was removed by evaporation at reduced pressure and the residue was treated with in 10% aqueous sodium bicarbonate. Insouble material was collected by filtration, washed with ether and dried to yield 2.9 (63%) of the desired product as a solid, mp 198.5-205C. An analytical sample was prepared by recrystallization from ethanol to yield a crystalline solid, mp 208.5-210.5C. IR and 1H NMR spectra were in agreement with the assigned structure.

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 2-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
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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 4224-69-5 as follows. Recommanded Product: Methyl 2-(bromomethyl)acrylate

General procedure: Into a round bottom flask charged with a magnetic stirbar was added 1.0 equiv. allylic bromide. This material was suspended in deionized water to produce a 1.0 M suspension. 1.5 volumetric equiv. of THF (w/respect to H2O) were then added with vigorous stirring, followed by 1.5 equiv. aldehyde and 1.1 equiv. indium powder. The reaction mixture was stirred for 12 hours, then was partitioned between EtOAc and deionized water. After separating the organic layer, the residual product was extracted with multiple portions (as necessary) of ethyl acetate. The combined organic layers was washed with brine, dried with Na2SO4, filtered, concentrated, and purified via column chromatography.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nicponski, Daniel R.; Tetrahedron Letters; vol. 55; 13; (2014); p. 2075 – 2077;,
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Reference of 42122-44-1,Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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.

c Methyl 2-(4-fluorophenyl)-pyrazolo[1,5-a]pyridine-3-carboxylate A stirred solution of methyl 3-(4-fluorophenyl)propiolate (8.02 g, 45 mmol) and 1-aminopyridinium iodide (10 g, 45 mmol) in dry acetonitrile (150 mL) was cooled to about 0 C. A solution of 1,8-diazabicycloundec-7-ene (13.7 g, 90 mmol) in dry acetonitrile (50 mL) was added dropwise over 1 h. The mixture was allowed to stir at room temperature for about 18 h. The reaction mixture was cooled in an ice bath for about 30 min and the precipitate was collected by filtration and washed with cold acetonitrile (10 mL). The solid was dried under reduced pressure to give the title compound as a white solid, 8.48 g (70%). 1H NMR (CDCl3) delta 8.50 (d, 1H, J=8.4 Hz), 8.18 (d, 1H, J=8.8 Hz), 7.78 (m, 2H), 7.42 (t, 1H, J=8.4 Hz), 7.13 (t, 2H, J=8.8 Hz), 6.97 (td, 1H, J=6.8, 1 Hz). MS (+ve ion electrospray) 271 (100), (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alberti, Michael John; Baldwin, Ian; Cheung, Mui; Cockerill, Stuart; Harris, Philip; Jung, David; Peckham, Gregory; Peel, Michael; Badiang, Jennifer; Stevens, Kirk; Veal, James; US2004/53942; (2004); A1;,
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Application of 369-26-6,Some common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, molecular formula is C8H8FNO2, 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.

Intermediate 37: 2-Propen-1-yl {5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate; Step A: Methyl 4-fluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate; To a solution of methyl 3-amino-4-fluorobenzoate (109 g, 644 mmol) in THF (2000 mL), saturated NaHCO3 (68 g, 805 mmol) was added. Then 2-propen-1-yl chloridocarbonate (93 g, 773 mmol) was added dropwise at 0 C. The mixture was stirred at rt for 2 h. The solution was extracted with EtOAc (500 mL¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product (160 g, 98%), which was used in the next step directly. 1H NMR (400 MHz, CDCl3) delta ppm 8.72-8.81 (m, 1H), 7.71-7.79 (m, 1H), 7.09-7.16 (m, 1H), 6.87-6.94 (br, 1H), 5.91-6.03 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5, 1H), 4.70 (d, J=10.5 Hz, 1H), 4.70 (d, J=5.5 Hz, 2H), 3.90 (s, 3H).

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Application of 145576-28-9, 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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cap N-8 At 0 C., to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed by the addition of 1 N diethylzinc in hexane (0.761 mL, 0.761 mmol). The reaction was stirred at 0 C. for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HCl, the organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 min gradient of 0-6% EtOAc in hexane to yield ethyl spiro[2.5]octane-6-carboxylate. 1H NMR (400 MHz, CDCl3) delta ppm 4.08-4.18 (2H, m), 2.32 (1H, tq, J=11.01, 3.53 Hz), 1.85-1.93 (2H, m), 1.53-1.74 (4H, m), 1.28-1.35 (2H, m), 1.22-1.28 (3H, m), 0.28 (2H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17-0.25 (2H, m).

The synthetic route of Ethyl 4-methylenecyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Hewawasam, Piyasena; Kadow, John F.; Lopez, Omar D.; Meanwell, Nicholas A.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Gupta, Samayamunthula Venkata Satya Arun Kumar; Srinivasu, Pothukanuri; Kumar, Indasi Gopi; Kumar, Ponugupati Suresh; Belema, Makonen; Fridell, Robert A.; Gao, Min; Lemm, Julie A.; O’Boyle, II, Donald R.; Sun, Jin-Hua; Wang, Chunfu; Wang, Ying-Kai; US2013/183269; (2013); A1;,
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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. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 2-amino-4-methoxylbenzoate

ii. 5-chloro-4-methoxyanthranilic acid (IXc, R=CH3) Treatment of methyl-4-methoxyanthranilate with sulfuryl chloride as described above afforded methyl-4-methoxy-5-chloroanthranilate, M.P., 197-200 C. in 90% yield. Saponification of methyl-4-methoxy-5-chloro anthranilate yielded 5-chloro-4-methoxyanthranilic acid in 64% yield, M.P., 210-3 C. Analysis, Percent Calc’d for C8 H8 ClNO3; C, 47.66; H, 4.00; N, 6.95 Found: C, 48.00; H, 4.11; N, 6.94.

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4287341; (1981); A;,
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18927-05-4, name is Methyl 3-Methoxyphenylacetate, 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. Formula: C10H12O3

[0333] AIBN (10 mg) was added to a solution of (3-Methoxy-phenyl)-acetic acid methyl ester (2g, 11MMOL) in [CCl4] (30ml). The solution was then heated to reflux and NBS (2.3g, 13MMOL) was added in portions. After complete addition the reaction mixture was refluxed for 4h. After cooling, solid residue was filtered off and the filtrate concentrated to yield product BROMO-(3-METHOXY-PHENYL)-ACETIC acid methyl ester, that was washed repeatedly with pet ether.

The synthetic route of 18927-05-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2003/105853; (2003); A1;,
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106614-28-2, name is Methyl 2,4-difluorobenzoate, 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. Computed Properties of C8H6F2O2

0.80mL fuming nitric acid was added dropwise 5mL concentrated sulfuric acid, stirred for 5min,Methyl 2,4-difluorobenzoate was added dropwise(1.50g, 8.71mmol, 1.0eq), and then reacted at room temperature for 30min, poured into ice water to precipitate a white solid, which was suction filtered to give a white solidProducts, dry, white solid product 1.8g.

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); A;,
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