Author: Jessica.F

Some common heterocyclic compound, 51122-91-9, name is Dimethyl Isopropylmalonate, molecular formula is C8H14O4, 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. HPLC of Formula: C8H14O4

EXAMPLE 1; 382 g (406 ml) of DMF were initially charged in a Schmizzo and 137 g (141 ml) of 1.0 eq. NaOMe (30% solution in methanol) were added. This mixture was then heated to 60 C. (+/-3 C.) and 131 g (0.753 mol) of dimethyl isopropylmalonate were metered in within one hour. Subsequently, a methanol/DMF mixture (201 g) was distilled off under pressure (300 mbar to 60 mbar) and a temperature of 60 C.Thereafter, at 80 C. (+/-3 C.), 86 g (79 ml, 0.779 mol, 1.03 eq.) of 1,3-dichloropropene were metered in within one hour and the reaction mixture was then heated at 80 C. (+/-3 C.) for two hours. The reaction mixture was heated to 140 C. and a 25% solution of LiCl (0.6 eq.) in methanol (19 g of LiCl in 58 g of methanol) was metered in within two hours, and the reaction mixture was heated at 140-142 C. for a further 6 hours, in the course of which a portion of the methanol was distilled off and approx. 1.5 mol of gas (mainly CH3Cl and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters. On completion of reaction, the solvent (DMF) and the excess methanol were distilled off substantially fully under reduced pressure. The remainder was admixed with 200 g of water, 89 g of 34% HCl and 200 g of MTBE, and the phases were separated. The organic phase was washed lx with 50 g of water and the solvent was removed under reduced pressure. Approx. 140 g of product were obtained, of which approx. 125 g were ester and 13 g the corresponding acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51122-91-9, its application will become more common.

Reference:
Patent; DSM Fine Chemicals Austria NFG GMBH & Co KG; US2008/207943; (2008); A1;,
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Synthetic Route of 35120-18-4,Some common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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 (5Z,8Z,1 1 Z,14Z,17Z)-icosa-5,8,1 1 ,14,17-pentaene-1 -thiol (305 mg, 1 .00 mmol) in dry DMF (10 mL) at 0C under inert atmosphere was added NaH (60% in mineral oil, 44 mg, 1 .1 mmol). After fifteen minutes ethyl 2-bromo-cyclobutane carboxylate (170 muIota_, 1 .05 mmol) was added and the mixture was stirred for 1 .5 hour at 0C. The reaction was quenched by addition of sat. aq. NH4CI (20 mL). Heptane (50 mL) was added, and the phases were separated. The water phase was extracted with heptane (2×25 mL). The combined organics were washed with water (25 mL) and brine (25 mL), dried (MgSC ), filtered and evaporated to give 409 mg of the title compound as a crude oil. Purification by flash chromatography on silica gel using isocratic elution (heptane:acetone 98:2) afforded 243 mg (56% yield) of the title compound as oil. 1 H- NMR (300 MHz, CDCI3): delta 0.95 (t, 3H), 1.27 (t, 3H), 1 .42 (d, 3H), 1.54 (m, 2H), 1.84 (m, 1 H), 1 .96-2.23 (m, 7H), 2.51 (m, 2H), 2.60 (m, 2H), 2.73-2.90 (m, 8H), 4.18 (m, 2H), 5.23-5.43 (m, 10H); MS (CI (CH4)): 471 [M+C3H5]+, 459 [M+C2H5]+, 431 [M+H]+, 385 [M-OEt]+, 357 [M-C02Et]+, 303 [R-S],+.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRONOVA BIOPHARMA NORGE AS; STEINEGER, Hilde; (38 pag.)WO2016/173923; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 606-45-1, name is Methyl 2-methoxybenzoate, 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 606-45-1, Product Details of 606-45-1

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C.

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

Reference:
Article; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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Synthetic Route of 37722-82-0, The chemical industry reduces the impact on the environment during synthesis 37722-82-0, name is Methyl 3-Hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

Methyl 1-oxaspiror2.5loctane-5-carboxylateTo a solution of trimethylsulfoxonium iodide (53.3 g, 242 mmol) in dry DMSO (300 ml.) under N2, was added sodium hydride (9.69 g, 242 mmol) portionwise over 30 min. This light yellow mixture was stirred at RT for 1 h. The reaction mixture was then cooled in an ice bath and treated with methyl 3-oxocyclohexanecarboxylate (29.0 g, 186 mmol) dropwise while maintaining a temperature at or below 27 C. The resulting reaction mixture was allowed to warm slowly to RT and stir overnight. The reaction was diluted with water and extracted with DCM. The combined organics were washed with water, dried over MgS04, filtered, and concentrated to provide methyl 1-oxaspiro[2.5]octane-5-carboxylate (31.8 g, 85 % yield) which was used without further purification. H NMR (400 MHz, CDCI3) delta 3.66 (s, 3H), 2.71 (m, 1 H), 2.65 (d, J = 1.76 Hz, 2H), 2.00 (dd J = 1 1.8, 13.6 Hz, 2H), 1.74 – 1.85 (m, 2H), 1.60 – 1.74 (m, 1 H), 1.40 – 1.56 (m, 2H), 1.17 – 1.32 (m, 1 H).

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 3-Hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); 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. 206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H10BrNO2

Example 134 5-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester To a stirred solution of 24.5 g (100 mmol) of the product of Example 133 in 100mL of pyridine was added 21.0 g (100mmol) of p-methoxybenzenesulfonyl chloride and the resulting mixture was heated to 80 C for 24 h. The reaction mixture was then quenched with ice cold water and acidified with concentrated HCl. The resulting mixture was extracted with chloroform, washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with diethyl ether, filtered and dried to provide 35g (84%) of the desired product as a brown solid. Electrospray Mass Spec 416, (M+H).

According to the analysis of related databases, 206548-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
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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. 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. Recommanded Product: 40872-87-5

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

The synthetic route of 40872-87-5 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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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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33689-29-1

Piperidine-1-carbonyl chloride (1.599 mL) was added to a solution of methyl 1-hydroxycyclopropanecarboxylate (1 mL) and DIEA (3.04 mL) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was wahed with iN HC1, water and brine, dried (Mg504), filtered andconcentrated. The residue was purified with silica gel gel to yield Cap L-7 Step a (0.75 g).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-amino-3-fluorobenzoate

4-Amino-3-fluorophenylhydrazide. Methyl 4-amino-3 -fluorob enzoate (250 mg, 1.48 mmols) was added to a 10 mL round bottom flask with stir bar, followed by addition of anhydrous hydrazine (500 1iL, 15.9 mmols). The reaction was then heated to 70C under N2 for 15 hours. After cooling, the mixture was poured into deionized water (40 mL), and the resulting precipitate was filtered and rinsed with additional water (50 mL) to give the product as a tan solid (130 mg, 52%). ?HNIVIR (400 MHz; DMSO-d6) = 9.41 (s, 1H), 7.48 (dd, J=12.8 Hz, 1.7 Hz, 1H), 7.43 (dd, J= 8.6, 1.7 Hz, 1H), 6.74 (t, J= 8.6 Hz, 1H), 5.66 (br, 2H),4.36 (br s, 2H). ?3C NIVIR (100 MFIz; DMSO-d6) 5= 165.4, 149.5 (d, J= 236.8 Hz), 139.5 (d,J 12.9 Hz), 124.0, 120.3 (d, J 4.8 Hz), 114.8 (d, J 3.9 Hz), 113.7 (d, J 19.6 Hz). ?9FNMR (376 IVIHz; DMSO-d6) = -136.96 (dd, J= 12.0, 9.2 Hz). Referenced againstCF3COOHat -76.55 ppm. (ESI) m/z calcd for C7H8FN3O (M) 169.0645, found 169.1001.

The synthetic route of 185629-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; RAIKHEL, Natasha, V.; HICKS, Glenn, R.; ZHANG, Chunhua; (107 pag.)WO2017/49016; (2017); A1;,
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Application of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of trans-Ethyl 4-hydroxycyclohexanecarboxylate

To a solution of ethyl 4-hydroxycyclohexanecarboxylate (5.00 g, 29.0 mmol) in dichloromethane (30 mL) was added 3,4-dihydro-2H-pyran (2.52 g, 29.0 mmol) and Amberlyst 15 (0.5 g). The reaction mixture was stirred at room temperature for 72 h, then another portion 3,4-dihydro-2H-pyran (1.89 g, 21.8 mmol) and Amberlyst 15 (0.5 g) was added, then after 5 h the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound as a yellow oil (9 g), which was used directly in the next step.

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; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Martin, Rainer E.; Mattei, Patrizio; Obst Sander, Ulrike; Richter, Hans; US2013/109718; (2013); A1;,
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