Category: esters-buliding-blocks

Application of 40872-87-5, 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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 Synthesis of 3-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester (13) A 100 mL three neck flask equipped with a thermocouple, condenser and stir bar was purged with argon. 3-Amino-4-chlorobenzoic acid methyl ester (5.0 g, 26.94 mmol), 2-cyclopentylethynyl-pyridine (5.528 g, 32.33 mmol), Pd(OAc)2 (181 mg, 0.81 mmol), DtBPF (767 mg, 1.62 mmol), K2CO3 (9.29 g, 67.35 mmol) and NMP (25 mL) were then charged. The reaction was heated to 130 C. and monitored by HPLC. The reaction was complete after 6 hours. The reaction was cooled to room temperature. DMC (11.4 mL, 134.69 mmol) and tetrabutylammonium bromide (TBAB) (0.868 g, 2.69 mmol) were added. The mixture heated to 130 C. HPLC showed less than 3% starting material remaining after 4.5 h. The mixture was filtered through a pad of diatomaceous earth. The black cake was washed with i-PrOAc (50 mL). Solution yield of this mixture was 78%. The crude product residue was dissolved in i-PrOAc (50 mL). The solution was washed with 0.3 N aqueous HCl three times (20 mL, then 2*15 mL). The organic phase was concentrated under vacuum. Propanol, water and 50% NaOH were added to the above residue. The reaction was heated to 90 C. for 1 h. HPLC showed that the reaction was complete. After the mixture was cooled to 50-60 C., diatomaceous earth and activated carbon were added. The mixture was stirred at 50 C. for 30 min and filtered to a 100 mL three neck flask through a pad of diatomaceous earth. The wet cake was washed with 18 mL of water/1-propanol 9/1. The mixture was then heated to 50 C. Acetic acid was added dropwise at this temperature. Precipitation was observed upon the addition. The suspension was then heated to reflux and held for 30 min. The mixture was slowly cooled to room temperature for 2 hours. The precipitate that formed was filtered. The wet cake was washed with 10 mL 1-propanol/water (2:1). The yellow solid was dried under vacuum for 2 days. 5.6 g product was obtained. The yield was 62% for three steps with 99.32 A % purity. 1H NMR (300 MHz, DMSO-d6) delta 8.80 (d, J=3.0 Hz, 1H), 8.14 (s, 1H), 8.00 (m, 1H), 7.77 (d, J=6.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.59 (d, J=6.0 Hz, 1H), 7.50 (m, 1H), 3.89 (s, 3H), 3.70 (s, 3H), 3.17-3.11 (m, 1H), 1.90-1.60 (m, 8H).

The synthetic route of Methyl 3-amino-4-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
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Some common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, 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. Safety of Ethyl (E)-3-Ethoxyacrylate

To a reactor was charged K3PO4 (4104 g granular, 19.3 moles), ethyl 3-amino-lH-pyrazole-4-carboxylate (2000 g, 12.9 moles), and DMF (18.8 kg) and the mixture was agitated. After 20 min, (?)- ethyl 3-ethoxyacrylate, (2230 g, 15.5 moles) was added and the mixture was heated to 110- 115 C internal temperature (IT). After the reaction was judged to be complete based on consumption of starting material, heating was ceased. The mixture was allowed to stir and cool overnight. Aqueous hydrochloric acid (3 M, 13 L) was added over ~ 2 h. DI water (6 L) was added and the mixture was allowed to stir overnight. The mixture was filtered through polypropylene filter cloth (PPFC) and the residue was washed with water (3 x 5 vol, 3 x 10 L). The solid was placed in trays and oven dried under vacuum at 55 C for 3 days and then 45 C for 4 days to constant wei ht of (2553 g 95.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5941-55-9, its application will become more common.

Reference:
Patent; ZHAO, Qian; SPENCER, Stacey; JIANG, Yutong; HAAS, Julia; EARY, Charles Todd; (352 pag.)WO2019/84285; (2019); 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. 130754-19-7, name is Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

500 mg of ethyl 2-(4-chlorophenyl)-2,2-difluoroacetate, adding 10 mL of methanol, 10 mL of water, 560 mg (10 mmol) of potassium hydroxide, stirring at room temperature for two hours, then evaporating methanol to remove water by rotary evaporation The layer was adjusted to pH 5 with hydrochloric acid to precipitate a white solid. Filtration in vacuo gave 270 mg of 2-(4-chlorophenyl)-2,2-difluoroacetic acid white powder. Used directly in the next step of the reaction.

According to the analysis of related databases, 130754-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhejiang University; Yang Chunhao; Shao Jimin; Zhu Weiliang; Xu Zhijian; Wang Meng; Chen Xinhuan; Hou Chuanwei; Liu Xia; Li Bo; Chen Kaixian; (47 pag.)CN105085433; (2019); B;,
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Some common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, molecular formula is C9H9ClO2, 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

General procedure: 5.2.1 5,6-Dichloro-1,3-dihydro-3-(4-chlorophenyl)-indole-2-one (3) Sodium hydrate 60% (2.85 g, 71.2 mmol) at -10 C and under nitrogen atmosphere was suspended in N,N-dimethylformamide (DMF) (45 ml) before being added to a solution of 1,2-dichloro-4-fluoro-5-nitrobenzene (5 g, 23.8 mmol) and methyl-4-chlorophenyl acetate (4.4 g, 23.8 mmol). in DMF (70 ml) The mixture was stirred at -5 C for 2 h and then allowed to warm up to room temperature. After quenching with ice, an aqueous solution of 10% NH4Cl was added and the mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using column chromatography on silica gel (hexane/EtOAc = 3/1) to give 1,2-dichloro-4-[2-(methy-l-4-chlorophenyl acetate)]-5-nitrobenzene (3.18 g, 36%) as a colourless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57486-68-7, its application will become more common.

Reference:
Article; Puleo, Letizia; Marini, Pietro; Avallone, Roberta; Zanchet, Marco; Bandiera, Silvio; Baroni, Marco; Croci, Tiziano; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5623 – 5636;,
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Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-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. Recommanded Product: 135484-83-2

Into a 1000-mE 3-necked round-bottom flask, was placed methyl 2-amino-4-bromobenzoate (5.0 g, 21.73 mmol, 1.00 equiv), a solution of sulfuric acid (20%) (20 mE) in water (100 mE). This was followed by the addition of a solution of NaNO2 (1.8 g, 26.09 mmol, 1.20 equiv) in water (20 mE) dropwise with stirring at 00 C., after stirred 1 hour at 00 C. To this was added a solution of iodopotassium (7.21 g, 43.43 mmol, 2.00 equiv) in water (30 mE) dropwise with stirring at 00 C. The resulting solution was stirred for 1 hour at 00 C. in a water/ice bath. The reaction was then quenched by the addition of 200 mE of water/ice. The resulting solution was extracted with ethyl acetate (100 mEx3) and the organic layers combined. The resulting mixture was washed with brine (100 mExl). The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/5). This resulted in 5.97 g (81%) of methyl 4-bromo-2-iodobenzoate as light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 135484-83-2, its application will become more common.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); A1;,
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These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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: 59247-47-1

A 3-neck flask was charged with NaOtBu (2.85 g, 28.6 mmol) and dry THF (50 mL) under nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (0.26 g, 0.28 mmol) and (S)-ToI- Binap (0.47 g, 0.69 mmol) were then added under nitrogen. After stirring for 15 min, l-(4- chlorophenyl)pentan-l-one (4.21 g, 21.0 mmol) was added, followed by tert-butyl 4- bromobenzoate (5.0 g, 19.1 mmol) under nitrogen. The mixture was heated at 600C for 8 hours. The mixture was diluted with heptane (100 mL) and poured into a solution of saturated NaHCO3 (aq) (60 mL) and ice (40 g). The resulting layers were separated, and the aqueous phase was back-extracted with methyl tert-butyl ether (50 mL). The combined organics were washed with saturated NaHCO3 (aq) then 10percent NaCl (aq). The organic solution was filtered through a bed of silica 60 (84 g, wetted with 1 :1 methyl tert-butyl ether/heptane), and washed with 1:1 methyl tert-butyl ether/heptane (600 mL). The combined filtrate was concentrated to afford an orange oil that was used directly for the next step: 1H NMR (500 MHz, CDCl3): delta 7.91 (d, J = 8.1 Hz, 2 H); 7.86 (d, J = 8.4 Hz, 2 H); 7.35 (d, J = 8.4 Hz, 2 H); 7.32 (d, J – 8.2 Hz, 2 H); 4.53 (t, J = 7.2 Hz, 1 H); 2.19-2.09 (m, 1 H); 1.85-1.76 (m, 1 H); 1.56 (s, 9 H); 1.35-1.18 (m, 2 H); 0.91 (t, J = 7.3 Hz, 3 H); LCl : 1.35 min. (M-tBu+H)+ 317.

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; LIN, Songnian; ZHANG, Fengqi; PARMEE, Emma, R.; DEWNANI, Sunita, V.; WO2010/88061; (2010); A1;,
Ester – Wikipedia,
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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. 3196-15-4, name is Methyl 2-bromobutyrate, A new synthetic method of this compound is introduced below., Formula: C5H9BrO2

Step 2: methyl 2-(2-((4-methylbenzoyl)imino-6-(methylcarbamoyl(2H)-yl)butanoate To a solution of N-methyl-2-(4-methylbenzamido)benzo[d]thiazol-6-carboxamide (185 mg, 0.57 mmol) prepared in Step 1 in N,N-dimethylformamide (2.0 mL) were added potassium carbonate (236 mg, 1.71 mmol) and methyl 2-bromobutyrate (98 uL, 0.86 mmol). The reaction mixture was stirred at 80 C. overnight and cooled to room temperature. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexaneethyl acetate=8/1?1/1, v/v) to give 160 mg of the titled compound as a white solid (Yield: 66%). 1H NMR (CDCl3, 400 MHz) delta 8.20 (s, 1H), 8.08 (d, 2H), 7.90 (d, 1H), 7.27 (d, 1H), 7.18-7.25 (m, 2H), 6.94-6.95 (m, 1H), 5.53 (m, 1H), 3.57 (s, 3H), 2.91 (d, 3H), 2.39-2.46 (m, 2H), 2.34 (s, 3H), 0.82 (t, 3H)

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; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 46064-79-3, 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. 46064-79-3 name is Methyl 3-amino-4-bromobenzoate, 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.

A mixture of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (16.1 g, 70 mmol), methyl 3-amino-4-bromobenzoate (21.9 g, 84 mmol), polyphosphoric acid (120 g) and dioxane (120 mL) was heated at 110 C for 4 hours. After cooling to room temperature, the mixture was poured into ice water, filtered and the filtrate was extracted with EtOAc (500 mL x3). The combined organic layers were dried, and concentrated to give crude residue, which was chromatographed on silica gel using gradient eluant of 20% to 50% ethyl acetate in petroleum ether to give the crude product. Then the crude product was dissolved in MeOH (1 L), TMSCl (150 mL) was added, and the mixture was stirred at reflux for 12 h. After cooling to room temperature, the solvent was evaporated and the residue was recrystallized from MeOH to afford methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (7.6 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-4-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; REN, Bo; WANG, Hexiang; WO2013/97226; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 90030-48-1, 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. 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

methyl 4-bromo-1-methyl-pyrazole-3-carboxylate (508 mg, 2.319 mmol), (3-methoxy- 3-oxo-propyl)sulfinyloxysodium (810 mg, 4.651 mmol), and copper(1+) (Iodide Ion (1)) (1.31 g, 6.878 mmol) were combined in degassed DMSO (3.048 mL). Nitrogen was bubbled through the reaction for another 5 min and then it was sealed and heated to 80 C. The reaction was heated for 48 h then cooled to room temperature. The reaction was diluted with ethyl acetate (25 mL) and NH4Cl (10 mL). A thick precipitate formed which was filtered and discarded. The layers were separated and the organics were washed with a saturated NH4Cl (30 mL) solution, a satd NaHCO3solution (30 mL), and brine (30 mL). The organics were dried over sodium sulfate and evaporated. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexanes to give methyl 4-(3-methoxy-3-oxo-propyl)sulfonyl-1-methyl-pyrazole-3- carboxylate (297 mg, 44%) ESI-MS m/z calc.290.05725, found 291.1 (M+1)+;Retention time: 0.32 minutes

The synthetic route of Sodium 3-methoxy-3-oxopropane-1-sulfinate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ABELA, Alexander, Russell; ALCACIO, Timothy; ANDERSON, Corey; ANGELL, Paul, Timothy; BAEK, Minson; CLEMENS, Jeremy, J.; CLEVELAND, Thomas; FERRIS, Lori, Ann; GROOTENHUIS, Peter Diederik, Jan; GROSS, Raymond, Stanley; GULEVICH, Anton; HADIDA RUAH, Sara, Sabina; HSIA, Clara, Kuang-Ju; HUGHES, Robert, M.; JOSHI, Pramod, Virupax; KANG, Ping; KESHAVARZ-SHOKRI, Ali; KHATUYA, Haripada; KRENITSKY, Paul, John; MCCARTNEY, Jason; MILLER, Mark, Thomas; PARASELLI, Prasuna; PIERRE, Fabrice Jean, Denis; SHI, Yi; SHRESTHA, Muna; SIESEL, David, Andrew; STAVROPOULOS, Kathy; TERMIN, Andreas, P.; UY, Johnny; VAN GOOR, Fredrick, F.; YOUNG, Tomothy, John; ZHOU, Jinglan; (398 pag.)WO2018/107100; (2018); A1;,
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Synthetic Route of 13412-12-9, A common heterocyclic compound, 13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, molecular formula is C6H11NO2, 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.

Step 2: 2-(4-Bromo-benzoyl)-3-oxo-butyric acid methyl ester To 3-methylamino-but-2-enoic acid methyl ester (5.0 g, 39.1 mmol) in THF (100 mL) was added pyridine (3.7 mL, 47 mmol). The mixture was cooled to 0 C., and 4-bromobenzoyl chloride (8.55 g, 39.1 mmol) in THF (30 mL) was added dropwise over 2 minutes. The reaction was warmed to room temperature over 1 hour and stirred overnight. Aqueous workup provided the 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; AMIRA PHARMACEUTICALS, INC.; US2012/258987; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics