Tag: M.W=100-200

Application of 15012-36-9, A common heterocyclic compound, 15012-36-9, name is Methyl 2,3-dimethylbenzoate, molecular formula is C10H12O2, 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.

Methyl 2,3-dimethylbenzoate was dissolved in concentrated sulfonic acid (10 mL). KNO3 (808 mg, 1.2 eq.) was added to the solution at 0 C., then slowly warmed to rt overnight. The reaction was quenched with water (80 mL), extracted with ethyl acetate (2¡Á80 mL). The organic layers were evaporated to give mixture of nitrated ester and acid (1:1). The mixture was redissolved in DMF (10 mL). K2CO3 (1.1 g) and iodomethane (0.5 mL) were added to the solution. The reaction was stirred at rt for three days, then diluted with water (80 mL). It was extracted with ethyl acetate (3¡Á80 mL) and evaporated. The residue was purified by column chromatography (EtOAc in hexanes=0-30% in 45 min) to give the desired nitrobenzoate ester. 1H NMR (300 MHz, DMSO) delta 8.31 (s, 1H), 8.24 (s, 1H), 3.86 (s, 3H), 2.46 (s, 3H), 2.40 (s, 3H).

The synthetic route of 15012-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; US2012/28923; (2012); A1;,
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Synthetic Route of 23426-63-3, A common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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.

General procedure: Toa solution of 1a (770 mg, 3.24 mmol) in DMF (20 mL) was added potassium carbonate (2.69g, 19.5 mmol).Thereaction mixture was stirred at ambient temperature for 30minutes. After addition of ethyl bromoacetate (1.08mL), the mixture was heated at 70oC for 2 hours. The mixture was cooled to ambient temperature andwater (60 mL) was added. The solution was extractedwith ethyl acetate (3 30 mL). The organic phase was washed withsaturated aqueous sodium chloride solution (2 ¡Á 15mL), dried over sodium sulfate, filtered and concentrated. The residue waspurified by column chromatography (silica gel, petroleum ether/ethyl acetate 5:1)to give the title compound (464 mg, 44% yield) as white solid.

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:
Article; Huang, Yaping; Sun, Geng; Wang, Pengfei; Shi, Rui; Zhang, Yanchun; Wen, Xiaoan; Sun, Hongbin; Chen, Caiping; Bioorganic and Medicinal Chemistry Letters; vol. 28; 17; (2018); p. 2957 – 2960;,
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Synthetic Route of 2396-84-1, These common heterocyclic compound, 2396-84-1, name is Ethyl sorbate, 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.

To a solution of diisopropyl amine (3.5 mL, 25.0 mmol) in dry THF (12 mL) cooled at -10 ¡ãC under a nitrogen atmosphere was added a solution of n-BuLi (10 mL, 2.5 M in hexanes, 25.0 mmol) followed by stirring for 30 min at the same temperature. The resultant LDA solution was then cooled to -78 ¡ãC, and, after adding HMPA (4 mL), was stirred for another 20 min at -78 ¡ãC.To the above prepared LDA-HMPA solution was added a solution of ethyl sorbate (8, 1.50 mL, 10.0 mmol) in dry THF (5 mL). After stirring at -78 ¡ãC for 1.5 h, the reaction was quenched by adding a mixed solution of water (22 mL) and acetic acid (4 mL). The reaction mixture was extracted with hexane (30 mL.x.3) and the combined organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered off, and concentrated under reduced pressure to give the crude deconjugate ester, which was used for next reaction without purification.

The synthetic route of 2396-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jinlong; Jiang, Xiuqing; Xu, Jingjing; Dai, Wei-Min; Tetrahedron; vol. 67; 1; (2011); p. 179 – 192;,
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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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 37466-90-3

General procedure: A flask was charged with o-phenylenediamine (1a; 54 mg, 0.5 mmol), hexafluoroacetylacetone (2; 125 mg, 0.6 mmol), Fe(OTf)3 (25 mg, 0.05 mmol), DMF (2.0 mL). The reaction was stirred at 80 C for 24 h, when the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (10 mL) was added to the mixure, and then extracted with EtOAc (3¡Á30 mL). The combined organic phase was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 3a (92 mg, 99%) as yellow solid.

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:
Article; Zhou, Yanmei; Shen, Guanshuo; Sui, Yuebo; Zhou, Haifeng; Tetrahedron Letters; vol. 57; 30; (2016); p. 3396 – 3399;,
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46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, 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. Product Details of 46193-76-4

To a solution of 4H-thiophene [3,2-b] pyrrole-5-carboxylic acid ethyl ester (4.24 g, 21.7 mmol) in DMF (20 mL) at room temperature was added K2CO3 (7.82 g, 56.6 mmol),Then iodomethane (2.52 g, 17.8 mmol) was added dropwise.The mixture was stirred at room temperature for 2 h.The reaction was quenched with water and extracted with EtOAc (3 ¡Á).The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel chromatography,Elution with 0-10% EtOAc in hexanes gave the title compound (3.96 g, 18.9 mmol, 87% yield).

The synthetic route of 46193-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Jiakesitu Drug Discovery Co., Ltd.; Beijing Jiakesi Drug Discovery Co., Ltd.; Fang Haiquan; Li Haijun; Yang Guiqun; Wang Yanping; Wu Lingjun; Li Qinglong; Du Yuelei; Zhang Lei; Hu Shaojing; (65 pag.)CN110407854; (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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7BrO2

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

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; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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Synthetic Route of 106614-28-2,Some common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Methyl 2,4-difluorobenzoate (1.00 g; 5.81 mmol), 4-fluorophenol (0.72 g; 6.39 mmol) and potassium carbonate (1.61 g; 11.62 mmol) in DMF (20 mL) are stirred at 90C for 4 hours. The reaction mixture is diluted with water and extracted three times with DCM. The combined organic layers are dried over MgSC , filtered and concentrated under reduced pressure. The residue is purified by RP-HPLC (ACN/water + TFA). Yield: 0.45 g (29%) ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1.15 min (method 1)

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
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Electric Literature of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

2-(3-Fluorophenyl)acetohydrazide (2.90 g, 17.22 mmol) and ethyl 2-ethoxy-2- iminoacetate (2.5 g, 17.22 mmol) in ethanol (30 mL) was stirred under nitrogen at rt overnight. The resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound ethyl 2-amino-2-(2-(2-(3- fluorophenyl)acetyl)hydrazono)acetate (3 g, 11.23 mmol, 65.2 % yield), which was used without further purification. MS (m/z) 268 (M+H+).

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JEONG, Jae U.; KANG, Jianxing; LEISTER, Lara Kathryn; ROMANO, Joseph J.; (82 pag.)WO2018/7973; (2018); A2;,
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Electric Literature of 33842-16-9, 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. 33842-16-9 name is Methyl benzo[d][1,3]dioxole-4-carboxylate, 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.

Method C; BenzoH ,31dioxole-4-carboxylic acidhydrazide (Intermediate compound); A mixture of 1 ,3-benzimidazole-4-carboxylic acid (3.0 g, 17,5 mmol), sulfuric acid (0.17 g, 1.75 mmol) and methanol (40 ml) was stirred at reflux for 15 h. The mixture of the intermediate benzo[1 ,3]dioxole-4-carboxylic acid methyl ester was allowed to reach room-temperature. Hydrazine monohydrate (8.5 g, 175 mmol) was added and the mixture was stirred at reflux for 15 h. The mixture was evaporated, water was added and the crystalline product was isolated by filtration. Yield 2.15 g (68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl benzo[d][1,3]dioxole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NeuroSearch A/S; PETERS, Dan; TIMMERMANN, Daniel, B.; NIELSEN, Elsebet, ?stergaard; DYHRING, Tino; CHRISTENSEN, Jeppe, Kejser; WO2010/86278; (2010); A1;,
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Related Products of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-isopropyl-5-(4-(6-(l,2,3,6-tetrahydropyridin-4- yl)benzo[d]thiazol-2-yloxy)piperidin-l-yl)-l,2,4-oxadiazole (Compound 43E, 95 mg, 0.223 mmol) and triethylamine (0.08 mL, 0.56 mmol) in CH2C12 (2mL) at 0 C was added methyl 3-(chlorosulfonyl)propanoate (62.5 mg, 0.335 mmol). The reaction mixture was stirred at 0 C for 15 min, then at rt overnight. The reaction mixture was quenched with sat. aq. aHC03 (2 mL) and extracted with CH2CI2 (3 x 3 mL). The combined organic layers were dried ( a2S04), filtered, and concentrated. The residue was purified by column chromatography (silica gel, CH2Cl2-EtOAc gradient 0 to 60% EtOAc) to afford methyl 3-(4-(2-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4- yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-l(2H)-ylsulfonyl)propanoate (75 mg, 0.13 mmol, 58% yield) as an off white solid. LCMS (m/z) =576 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-(chlorosulfonyl)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
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