Author: Jessica.F

Synthetic Route 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.

To a solution of ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate (20 g, 53 mmol) in DMF (100 mL) at 0 C. was added KOtBu (7.73 g, 69 mmol). The mixture was stirred at 0 C. for 45 minutes, then tert.-butyl 4-bromobutanoate (15.4 g, 69 mmol) was added at 0 C. The reaction mixture was allowed to warm to room temperature and stir overnight. The mixture was portioned between ether and saturated aqueous NH4Cl. The organic solution was washed with water and saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The residue was taken into hot cyclohexane. The mixture was allowed to stand for 72 hours. The solvent was decanted and the residue was washed with cold cyclohexane. The solid was then dried under high vacuum to yield 4-(3-tert.-butoxycarbonyl-propoxy)-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-1a: 20.8 g). 1H NMR (400 MHz, CHLOROFORM-D) ppm 1.4 (s, 9H), 1.4 (t, J=7.1 Hz, 3H), 1.9 (m, 2H), 2.3 (t, J=7.5 Hz, 2H), 4.0 (t, J=5.9 Hz, 2H), 4.4 (q, J=7.1 Hz, 2H), 7.2 (m, 2H), 7.2 (m, 2H), 7.4 (m, 3H), 7.5 (m, 1H); m/z=519.0 (M+1).

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

Reference:
Patent; Pfizer Inc; US2006/241100; (2006); 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. 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate

A solution of dimethyl bicyclo [2.2.1] heptane-1, 4-dicarboxylate (500 mg, 2.356 mmol) and LiOH (169 mg, 7.07 mmol) in water (20 mL) and MeOH (10 mL) was stirred at RT for 48 hours. The solution was poured into 1 N HCl and extracted with EtOAc. The combined organic was dried over Na2SO4and concentrated in vacuo to give crude title compound.

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H11NO3

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (M+H) +

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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
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Application of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, 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 185312-82-7, COA of Formula: C8H6BrClO2

Reference Example 12 4-bromo-2-chlorobenzyl alcohol Methyl 4-bromo-2-chlorobenzoate (477 g) of Reference Example 11 was dissolved in a mixed solution of ethanol (3000 mL) and water (680 mL), calcium chloride (212.2 g) was added at 10C, and the mixture was stirred for 30 min. To the solution was added sodium borohydride (144.7 g) by portions so that the inside temperature would not exceed 25C, and the mixture was stirred at room temperature for 5 hr. 1M Hydrochloric acid (5100 mL) was added dropwise to the reaction mixture, and the reaction solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue. After partitioning and extraction, the organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (399 g) as white crystals. 1H-NMR(CDCl3)delta(ppm):1.87(1H, t, J=5.8Hz), 4.74(2H, d, J=5.8Hz), 7.38(1H, d, J=8.2Hz), 7.42(1H, dd, J=1.8, 8.2Hz), 7.53(1H, d, J=1.8Hz).

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; Mitsubishi Tanabe Pharma Corporation; EP2017257; (2009); A1;,
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These common heterocyclic compound, 2065-23-8, name is Methyl 2-phenoxyacetate, 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. category: esters-buliding-blocks

8.3 g of compound 2 was dissolved in 100 mL of methanol/water (9:1).12 g of lithium hydroxide was added. The reaction system was heated to 50 C and stirred for 12 h.The reaction was followed by TLC. After the reaction was over, the reaction system was added to 300 mL of ice water.Then, pH = 1 was adjusted with 6 mol/L HCl, and a large amount of white solid was formed. filter,A white solid was collected and dried in vacuo to give 6.8 g of white solid. The yield was 90%.

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

Reference:
Patent; Liaocheng University; Lei Kang; Chen Ke; Wang Shiben; Hua Xuewen; Liu Yang; Xu Xiaohua; (8 pag.)CN108570028; (2018); A;,
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Synthetic Route of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140°C for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and the extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane: ethyl acetate = 4:1 -> 2:1) gave 136 mg (58percent) of the desired compound as a colorless amorphous product. 1H NMR (400 MHz, CDCl3) delta 1.77-1.86 (1H, m), 2.11-2.19 (1H, m), 2.60-2.67 (1H, m), 2.71 (3H, s), 3.21-3.38 (4H, m), 3.54 (2H, t, J= 6.1 Hz), 3.87 (3H, s), 6.26 (1H, t, J = 6.1 Hz), 6.78 (1H, t, J = 7.9 Hz), 6.82 (1H, d, J = 8.6 Hz), 7.32-7.36 (1H, m), 7.41 (2H, d, J = 8.6 Hz), 7.63 (1H, dd, J = 1.8, 7.3 Hz), 7.85 (2H, d, J = 8.6 Hz). FAB+(m/z): 470 (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; KYORIN PHARMACEUTICAL CO., LTD.; EP1780210; (2007); A1;,
Ester – Wikipedia,
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Some common heterocyclic compound, 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, molecular formula is C8H8ClNO2, 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. Computed Properties of C8H8ClNO2

1 g of methyl 4-amino-2-chlorobenzoate was cooled to 0C in DCM with 485 muL of Pyridine before Methanesulfonyl Chloride was added dropwise. The reaction was allowed to warm to room temperature and stir overnight. Solvent was concentrated and the crude material was dissolved in Ethyl Acetate and extracted with saturated bicarbonate solution and then brine. The crude material was dried over Magnesium Sulfate, filtered and concentrated to give 1.54 g of methyl 2-chloro-4-(methylsulfonamido)benzoate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 46004-37-9, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CURIS, INC.; WO2009/126863; (2009); A2;,
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Synthetic Route of 13671-00-6, 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. 13671-00-6, name is Methyl 2,6-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

a) Methyl 2-JZUORO-6-PHENOXYBENZOATE Methyl 2,6-difluorobenzoate (2 g), phenol (1.09 g), caesium carbonate (3.79 g), and dimethylformamide (10 mL) were loaded in a 100 mL round bottom flask and the resulting suspension heated to 80C for 6 h. After cooling the reaction to room temperature, water (30 mL) was added and the mixture extracted with dichloromethane (2 x 30 mL). The combined organic extracts were washed with brine (30 mL), dried (magnesium sulphate), filtered and evaporated in vacuo. The residue was purified by column chromatography (Silica: DICHLOROMETHANE/HEXANE 5: 2) to give the titled compound as a clear oil (1.7 g)

The chemical industry reduces the impact on the environment during synthesis Methyl 2,6-difluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2004/113303; (2004); A1;,
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Application of 18448-47-0, These common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, 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: 4-Trifluoromethylbenzonitrile oxide (4) was generated as follows: a solution of the corresponding chloroxime (0.25g, 1.12mmol) in dry dichloromethane was passed through an Amberlyst-21 column and added dropwise over 30min to the solution of a dipolarophile in dry dichloromethane, and the solution was stirred overnight at room temperature. Water was added, organic layer was separated and the aqueous one extracted with dichloromethane. The combined organic layers were dried (MgSO4) and the product was purified by flash column chromatography.

Statistics shows that Methyl cyclohex-1-enecarboxylate is playing an increasingly important role. we look forward to future research findings about 18448-47-0.

Reference:
Article; Gucma, Miros?aw; Go??biewski, W. Marek; Michalczyk, Alicja K.; Journal of Molecular Structure; vol. 1060; 1; (2014); p. 223 – 232;,
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