Month: July 2021

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

(32d) methyl 4-acetyl-3-fluorobenzoate Cobalt (II) bromide (976 mg, 4.46 mmol) and zinc (4.96 g, 75.8 mmol) were suspended in acetonitrile (40 mL) and, under a nitrogen atmosphere, allyl chloride (1.10 mL, 13.4 mmol) and trifluoroacetic acid (0.205 mL, 2.68 mmol) were added, and the mixture was stirred for 10 min. A solution (60 mL) of methyl 4-bromo-3-fluorobenzoate (10.4 g, 44.6 mmol) produced in Example 32 (32c) and acetic anhydride (4.64 mL, 49.1 mmol) in acetonitrile was added, and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added 1.0 M hydrochloric acid (2.7 mL), and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 10:1, V/V). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (1.78 g, yield 20%). 1H-NMR (CDCl3, 400 MH) delta: 2.68 (3H, d, J=4.6 Hz), 3.96 (3H, s), 7.77-7.95 (3H, m).

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; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
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These common heterocyclic compound, 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, 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. Formula: C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

The synthetic route of Methyl 3-(4-aminophenyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27492-84-8

Synthesis of 4-(2-Chloro-ethylamino)-2-methoxy-benzoic acid methyl ester 16; Methyl 4-amino-2-methoylbenzoate (2 g, 11.04 mmol, 1 eq) was dissolved in methanol (30 ml) and a 1:1 mixture (2 ml) of 6M aq. HCl and methanol was added. Chloroacetaldehyde (50percent in water, 2.08 ml, 13.27 mmol, 1.2 eq) was added and the mixture was cooled to 0° C. NaBH3CN (0.78 g, 12.37 mmol, 1.12 eq) was added in portions over 2 min and the mixture was stirred for 5 days at ambient temperature. The mixture was poured into sat. aq. NaHCO3 (100 ml) and DCM (100 ml) was added, the pH was adjusted to 7-8 with dil. aq. HCl and the organic layer was poured off. The aqueous layer was then extracted with DCM (2.x.50 ml) and the combined organic layers were washed with water (2.x.100 ml), were washed with brine (50 ml), were dried over Na2SO4, filtered and the solvent was removed in vacuo. The product was purified via column chromatography eluted with a gradient from 1:1 to 1:3 CyH:EtOAc (Rf product=0.5, Rf SM=0.35 in 1:3 CyH:EtOAc, UV, KMnO4). This gave 1.968 g (73percent) of white solid. 1H-NMR (CDCl3) 500 MHz: delta (ppm)=3.55 (2H, br.quart, J=5.1 Hz, ClCH2CH2), 3.71 (2H, t, J=5.9 Hz, ClCH2CH2), 3.82 (3H, s, COCH3), 3.86 (3H, s, COOCH3), 4.48 (1H, br.s, ClCH2CH2NH), 6.13 (1H, d, J=1.9 Hz, CCHCN), 6.19 (1H, dd, J=2.0 Hz, J=8.6 Hz, CCHCHCN), 7.77 (1H, d, J=8.6 Hz, CCHCHCN). 13C-NMR (CDCl3) 125 MHz: delta (ppm)=43.1 (CH2), 44.8 (CH2), 51.4 (CH3), 55.8 (CH3), 96.1 (CH), 104.1 (CH), 108.8 (C), 134.3 (CH), 152.2 (C), 161.8 (C), 166.1 (CO). IR Spectrum; evaporated film: v(cm-1)=3361, 2950, 2840, 1700, 1607, 1526, 1346, 1255, 1182, 1085. MS-ES (negative): 242.1 (M-H+), 244.1 (M-H+). MS-ES (positive): 244.1 (M+H+), 246.1 (M+H+).

According to the analysis of related databases, 27492-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Desreumaux, Pierre; Bellinvia, Salvatore; Chavatte, Philippe; Baroni, Sergio; US2011/39808; (2011); 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. 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Amixture of methyl 5-bromo-2-methoxy-4-methylbenzoate (41,100 mg, 0.39 mmol), Zn(CN)2 (31.7 mg, 0.27 mmol), xantphos(2.23 mg, 0.0039 mmol), Pd2(dba)3 (21.2 mg, 0.0232 mmol) andN,N,N’,N’-tetramethylenediamine (8.97 mg, 0.0772 mmol) inanhydrous DMF (1 mL) was placed in a 5 mL tube. Nitrogen wasbubbled through the mixture for 5 min, then the tube was immediatelysealed and heated to 160 C (under microwave irradiations)for 200 s. The mixture was then cooled down to room temperatureand diluted with EtOAc (30 mL). The organic phase was washedwith brine (3*10 mL), dried over Na2SO4, filtered, and concentratedunder reduced pressure. The crude was purified by flash columnchromatography on silica gel (EtOAc in petroleum ether, 0%e50%)to afford the title compound (73 mg, 92%) as a white solid. 1H NMR(400 MHz, CDCl3): delta 8.09 (s, 1H), 6.89 (s, 1H), 3.97 (s, 3H), 3.90 (s,3H), 2.59 (s, 3H). MS m/z 206 [M+H]+.

The synthetic route of 39503-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lovering, Frank; Morgan, Paul; Allais, Christophe; Aulabaugh, Ann; Brodfuehrer, Joanne; Chang, Jeanne; Coe, Jotham; Ding, WeiDong; Dowty, Heather; Fleming, Margaret; Frisbie, Richard; Guzova, Julia; Hepworth, David; Jasti, Jayasankar; Kortum, Steve; Kurumbail, Ravi; Mohan, Shashi; Papaioannou, Nikolaos; Strohbach, Joseph W.; Vincent, Fabien; Lee, Katherine; Zapf, Christoph W.; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 606 – 621;,
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Application of 57381-59-6, These common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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.

Sequentially add tri-tert-butylphosphine (88 mg, 0. 437 mmol) in anhydrous 1, 4- dioxane (1 mL), diisopropylethylamine (1. 5 mL, 8. 74 mmol), 5-bromo-2-fluorobenzoic acid methyl ester, (prepared as described in PREPARATION 42), (1. 69 g, 7. 28 mmol) and a solution of 5-ethynylnicotinonitrile, (prepared as described in PREPARATION 4), (0. 93 g, 7. 28 mmol) in anhydrous 1, 4-dioxan (4 mL), to a stirring mixture of dichloro (benzonitrile) palladium (II) (84 mg, 0. 218 mmol) and copper (I) iodide (28 mg, 0. 146 mmol) in anhydrous 1, 4-dioxan (1 mL) under nitrogen. Stir for 2 h and concentrate. Purify the residue twice by silica gel chromatography, eluting with 10 : 90 ethyl acetate : hexanes, to give the title compound as a white solid (0. 9 g, 44%). 1H NMR (400 MHz, CDCl3) 6 1. 48 (s, 3H), 3. 87 (s, 3H), 7. 07-7. 12 (m, 1H), 7. 58-7. 62 (m, 1H), 7. 96-7. 98 (m, 1H), 8. 06 (dd, J = 2. 7 Hz, J = 6. 5 Hz, 1H), 8. 74 (br s, lH), 8. 84 (br s, 1H) ; MS (ES) : m/z = 280. 9 [M+H] +.

The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
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Application of 3153-37-5,Some common heterocyclic compound, 3153-37-5, name is Methyl 4-chlorobutyrate, molecular formula is C5H9ClO2, 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.

A mixture of the product from step d (100 mg, 0.406 MMOL), K2CO3 (120 mg, 0.88 MMOL), Kl (cat.) and methyl 4-chlorobutyrate (140 mg, 1.02 MMOL) in acetone (2 ML) is heated at reflux for 8 hours. 1N sodium hydroxide (2 ML) is then added, and the mixture is heated at 60C for 2 hours. The reaction mixture is poured into water, acidified to pH 1 and then extracted with ethyl ether. The organic phase is washed with water and concentrated. Recrystallisation from cyclohexane of the residue obtained gives the expected product (40 mg). m. p. =81C 1H NMR-CDCI3- (PPM) : 0.87 (3H, m); 1.12-1. 43 (6H, m); 1.53 (2H, m); 2.09 (2H, m); 2.37-2. 68 (4H, m); 2.85 (2H, m); 3.23 (2H, m); 3.59 (2H, m); 4.03 (2H, m); 6.99 (1 H, s); 7.40 (1 H, s).

The synthetic route of 3153-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; WO2004/63148; (2004); 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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H12O2

Methyl 3,5-bis[[bis(2-pyridylmethyl)amino]methyl]benzoate (3) Methyl 3,5-bis(bromomethyl)-benzoate (500 mg, 1.6 mmol) and di-(2-picolyl)-amine (800 mg, 725 muL, 4 mmol) were dissolved in ACN followed by the addition of dry K2CO3 (1.1 g, 7.9 mmol). The reaction mixture was refluxed overnight under reflux condenser equipped with a CaCl2 tube. The reaction mixture was filtered and filtrate was evaporated under reduced pressure. Yellow residue was purified by flash chromatography (Al2O3 neutral, firstly AcOEt was used to elute impurities and then MeOH/AcOEt=1:9 (v/v)) affording a pure product as a yellow oil. Yield: 850 mg (95%). 1H NMR (500 MHz, CDCl33) delta 8.51 (m, 4H), 7.94 (d, J=1.5 Hz, 2H), 7.70 (s, 1H), 7.61 (m, 8H), 7.12 (m, 4H), 3.92 (s, 3H), 3.81 (s, 8H), 3.73 (s, 4H). 13C NMR (101 MHz, CDCl3) delta 197.9, 167.1, 159.5, 148.9, 139.7, 136.2, 133.8, 130.2, 128.7, 122.8, 121.9, 60.1, 58.2, 52.0. MS (ESI, m/z): calculated: 558.7 observed: 559.5 [M+H]+.

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Modpro AB; Baltzer, Lars; Slosarczyk, Adam; Bergquist, Jonas; Virtanen, Anders; (86 pag.)US9377466; (2016); B2;,
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These common heterocyclic compound, 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, 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. HPLC of Formula: C7H12O3

Di-terf-butyl azodicarboxylate (4.8 g, 20.809 mmol) was added portionwise to a solution of 3-methoxy-5-nitrophenol [7145-49-5] (3.2 g, 18.917 mmol), ethyl 2-(hydroxymethyl)cyclopropanecarboxylate 6a (3 g, 20.809 mmol), and PP i3 (5.46 g, 20.809 mmol) in THF (150 mL). The reaction was stirred at room temperature under N2 for 18 h. The solution was concentrated under reduced pressure. The crude residue was purified by preparative LC (irregular SiOH 20-45 muetatauiota, 220 g, heptane/EtOAc from 85/15 to 75/25). The pure fractions were combined and concentrated under reduced pressure to give methyl 2-((3-methoxy-5- nitrophenoxy)methyl)cyclopropanecarboxylate 6b (1 .4 g).

The synthetic route of Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); A1;,
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Electric Literature of 35179-98-7,Some common heterocyclic compound, 35179-98-7, name is Chloromethyl ethyl carbonate, molecular formula is C4H7ClO3, 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 100 ml of one-necked flask, 0.698g of material, 0.162g of potassium carbonate, 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at room temperature for 20 minutes. Then 0.702g of chloromethyl ethyl carbonate was added and the mixture was reacted at 45-50C for 16 hours. After the reaction was completed, the mixture solution was filtered, and 30ml of water was added into the filtrate. The resulting mixture was extracted with 30ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.854g of oil, which was directly used in the next reaction without purification. 10ml of dioxane and 5ml of 4mol/L HCl were added and the resulting mixture was reacted at room temperature for 16 hours. The reaction was stopped and the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution went turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.420g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl] imidazole-5- carboxylic acid, 1-[(ethoxycarbonyl)oxy] methyl ester. 1H-NMR (CDCl3) delta H (ppm) 0.92(t,3H,J=17.5), 1,23(t,3H,J=14.0), 1.37(m,2H,J=34.2), 1.73(m,2H,J=30.8), 2.69(t,2H,J=15.5), 4.13(q,2H,J=15.7), 5.58(s,2H), 5,89(s,2H), 6,99-7.61(8H), 8.16(d,1H,J=6.1) ESI(-): 539.1 Mp:164.5-160C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Chloromethyl ethyl carbonate, its application will become more common.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP1988090; (2008); A1;,
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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 20330-90-9 as follows. Computed Properties of C10H9ClO4

A mixture of dimethyl 5-chloroisophthalate (6.84 g, 30 mmol), in methanol (150 mL) was treated with 1M sodium hydroxide (27 mL, 27 mmol) and the reaction stirred at room temperature for 16 hours. The mixture was concentrated under vacuum and the resulting residue was dissolved in water. The mixture was extracted with ethyl acetate three times. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-chloro-5-(methoxycarbonyl)benzoic acid (4.8 g, 75%).

According to the analysis of related databases, 20330-90-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
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