Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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 148547-19-7, Formula: C9H9BrO2

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 3 g; 13.10 mmol; 1 eq.), 2-(trifluoromethyl)phenylboronic acid (Aldrich 393606; 2.74 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.05 g; 65.48 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) in toluene (15 ml_) and water (15 ml_) was refluxed for 3 hours. The resulting mixture was filtered through a short pad of Celite, which was further washed with toluene. After evaporation of the solvent, the residue was taken up in ethyl acetate and washed successively with sat. aq. NaHCC>3, water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (3.7 g, 96%) as a brown oil. HPLC (Method A) : Rt 5.34 min (purity 70.9%). LC/MS : 294.9 (M+H)+.

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; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 820236-81-5, name is Methyl 2-bromo-6-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6BrFO2

Synthesis of methyl 2-[4-[2-[4-(2,2-dimethylpropyl)-1-trityl-imidazol-2-yl]ethyl]phenyl]-6-fluoro-benzoate (14): a mixture of 13 (5.17 g, 9.17 mmol), bis-pinacolatodiboron (3.06 g, 12.1 mmol), [1,1?-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (0.38 g, 0.47 mmol) and KOAc (2.74 g, 27.9 mmol) in dioxane (100 mL) was stirred under reflux for 8 h. After the reaction mixture was concentrated, the residue was dissolved in EtOAc and water, then filtered through a Celite pad. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by column chromatography (hexane:EtOAc = 5:1) to provide the boronate ester as a pale yellow solid (5.17 g, 92%). A mixture of the boronate ester (8.92 g, 14.6 mmol), methyl 2-bromo-6-fluoro-benzoate (4.42 g, 19.0 mmol), Pd(PPh3)4 (1.69 g, 1.46 mmol) and 2 M Na2CO3 (22 mL, 44 mmol) in DMF (170 mL) was stirred at 100 C for 7 h. The mixture was concentrated and diluted in ethylacetate, washed with water, dried (Na2SO4), concentrated and purified by column chromatography (hexane:EtOAc = 3:1) to provide 14 as a pale yellow amorphous (6.54 g, 71%) 1H NMR (CDCl3) delta: 7.43-7.36 (1H, m), 7.35-7.29 (9H, m), 7.16-7.10 (9H, m), 7.10-7.04 (1H, m), 6.84 (2H, d, J = 8.2 Hz), 6.35 (1H, s), 3.61 (3H, s), 2.45-2.40 (4H, m), 2.31-2.25 (2H, m), 0.93 (9H, s). MS (APCI) m/z: 637 (M+H)+.

According to the analysis of related databases, 820236-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kiyotsuka, Yohei; Shimada, Kousei; Kobayashi, Shozo; Suzuki, Masanori; Akiu, Mayuko; Asano, Masayoshi; Sogawa, Yoshitaka; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Takamori, Hideo; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4205 – 4210;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2435-36-1, The chemical industry reduces the impact on the environment during synthesis 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, I believe this compound will play a more active role in future production and life.

Step B: Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate. n-Butyllithium (2.5 M in hexane, 419.0 mL, 1048 mmol) was added slowly to a solution of diisopropylamine (152 mL, 1090 mmol) and anhydrous THF (1000 mL) at -78 C (dry ice/acetone) underN2. Next, the reaction was stirred for 0.5 hours at 0 C before cooling to -78 C. DIVIPU (404 mL, 3350mmol) was added via an addition funnel. Then a solution of dimethyl cyclopentane-1,3- dicarboxylate (78.0 g, 419 mmol) and anhydrous THF (300 mL) was added slowly via an addition funnel. The reaction was warmed to 0 C and stirred for 30 minutes, then cooled to -78C and treated with a solution of 1-bromo-2-chloroethane (59.0 mL, 712 mmol) and anhydrous THF (200 mL). The reaction was allowed to warm slowly to room-temperature and was stirred for 12 hours at room-temperature. The reaction was quenched with saturated aqueous ammonium chloride (400 mL). The reaction was diluted with ethyl acetate (500 mL), the organic layer separated, and the aqueous layer was further extracted with ethyl acetate (2 x 500 mL). The combined organic extracts were washed with brine (2 x 300 mL), dried overanhydrous MgSO4, filtered, and concentrated to dryness. The residue was filtered through a pad of silica gel and washed with ethyl acetate (2000 mL). The filtrate was concentrated to dryness and the residue was purified by flash column chromatography (petroleum ether/ethyl acetate, 30 :1 to 20 :1, gradient elution) to provide the title compound (48.5 g, 54%) as white solid. ?H NIVIR (400MHz, CDC13): 3.69 (s, 6H), 2.08 – 1.99 (m, 4H), 1.91 (s, 2H), 1.73 – 1.63 (m, 4H)

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, Dimethyl cyclopentane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis M.; CHAI, Wenying; KOUDRIAKOVA, Tatiana; KRAWCZUK, Paul J.; KREUTTER, Kevin D.; LEONARD, Kristi; RIZZOLIO, Michele C.; SEIERSTAD, Mark; SMITH, Russel C.; TICHENOR, Mark S.; VENABLE, Jennifer D.; WANG, Aihua; (452 pag.)WO2018/112382; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 53518-15-3, 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. 53518-15-3 name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, 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 vial was charged with S5 (9 mg, 0.011 mmol), 7-amino-4-(trifluoromethyl) coumarin (7 mg, 0.033 mmol, 3 eq.), HATU (12 mg, 0.033 mmol, 3 eq.), DIEA (19 1iL, 0.11 mmol, 10 eq.) and DIvIF (300 1iL). Contents were stirred at room temperature and ambient atmosphere for 24 h, after which the solvent was concentrated to dryness, and the crude product was purified by silica gel chromatography (0-5% MeOH/DCM, linear gradient) to afford PC-3F549-exHT (2 mg, 18%).?H NMR (CDC13, 400 MHz) 8.05 (d, J 7.9 Hz, 1H), 7.92 (d, J= 8.0 Hz, 1H), 7.49 (m, 2H), 7.30 (dd, J 8.9, 2.1 Hz, 1H), 7.17 (d, J= 2.1 Hz, 111), 6.79 (s, 1H), 6.65 (s, 1H), 6.57 (d, J 8.6 Hz, 2H), 6.12 (d, J 2.3 Hz, 2H), 6.02 (dd, J= 8.6, 2.3 Hz, 2H), 5.23 (s, 1H), 4.14 (s, 2H), 3.89 (t, J 7.3 Hz, 811),3.67 -3.50 (m, 18H), 3.45 (t, J 6.6 Hz, 211), 3.33 (d, J= 5.6 Hz, 2H), 2.37 (p, J= 7.2 Hz, 4H),1.77 (p,J= 6.7 Hz, 2H), 1.60 (d, J= 14.6 Hz, 2H), 1.44 (q, J 8.1, 6.8 Hz, 2H), 1.37 (d, J 7.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; HOWARD HUGHES MEDICAL INSTITUTE; LAVIS, Luke; JRADI, Fadi, M.; (109 pag.)WO2018/182811; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2475-80-1, name is Methyl 2-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-amino-5-methoxybenzoate

The MicroKans were washed once with DCE prior to addition of reagents. A solution of 1,3-diisopropylcarbodiimide (0.1 M) and 1-hydroxy-7-azabenzotriazole (0.2 M) in NMP (0.75 mL/MicroKan) was prepared. The solution was added to the MicroKans in a round bottom flask, and the mixture was degassed. The round bottom flask was put on a shaker for two hours. Then methyl 2-amino-5-methoxybenzoate (0.4 M) was added. The flask was heated to 70 C. for 48 hours, and the MicroKans were washed with DMF (3×), 8:1:1 THF/H2O/AcOH (2×), and THF (3×) to afford 9D-1.

The synthetic route of 2475-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kick, Ellen K.; Lawrence, R. Michael; Fink, Brian E.; Misra, Raj N.; Vite, Gregory D.; US2006/135619; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-amino-5-bromobenzoate

To a solution of compound 28-6 (2.1 g, 9.17 mmol) in THF (20 mL) was added a aqueous solution of NaOH (2.1 g, 20 mL). At the end of the addition, the mixture was stirred at 60 C overnight. After the reaction was completed, the THF solvent was removed. The residue was dissolved in EtOAc (50 mL) and washed with water (50 mL x 3). The combined aqueous phase was adjusted to pH 4 with hydrochloric acid (1 M) and the solid was precipitated. The resulting mixture was filtered to give the title compound as a pale yellow solid (1.42 g, 72%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 217 [M+H] +; and ln NMPv (400 MHz, CDC13) delta (ppm): 7.59 (d, 1H, J= 8.0 Hz), 6.96 (d, 1H, J= 1.6 Hz), 6.64 (dd, 1H, J= 8.0 Hz, 2.0 Hz).

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 52727-57-8.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; LI, Shifeng; FU, Changping; HU, Bailin; WU, Xiwei; TANG, Changhua; WO2014/82380; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 15964-79-1, A common heterocyclic compound, 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, molecular formula is C11H14O4, 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.

l-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-l,3-dione; Sodium hydride (60% dispersion, 3.80 g, 95.1 mmol) was added portionwise to methyl 2-(3,4-dimethoxyphenyl)acetate (10 g, 47.6 mmol) in Et2O (100 ml) at O0C. A solution of 4′-bromoacetophenone (9.48 g, 47.6 mmol) in Et2O (50 ml) was added dropwise over 1 h. The mixture was heated at reflux for 16 h, cooled, poured into ice/HCl (2 M), extracted with Et2O (3 x 100 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was crystallized from MeOH to give the title compound (9 g, 50 %) as a tan powder.

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; ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D’OPTIQUE); ALPHAMICRON, INC.; WO2008/30226; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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. Computed Properties of C9H12N2O2

General procedure: Ethyl-3-amino-4-(2-substituted amino)benzoate, 3 (1 mmol) and various sodium bisulfite adducts, 4 (1.5 mmol) were dissolved in DMF (5 mL). The reaction mixture was stirred at 90 C under N2 atmosphere for 24-48 h. After completion of reaction (evident by TLC), the reaction mixture was diluted in ethyl acetate (25 mL) and washed with water (10 mL×3). The organic layer was collected, dried over Na2SO4 and evaporated under reduced pressure to afford crude products. Final compounds 5-7 were obtained in 38-90% yields after recrystallization from ethanol or column purification.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoon, Yeong Keng; Ali, Mohamed Ashraf; Wei, Ang Chee; Choon, Tan Soo; Ismail, Rusli; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 614 – 624;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2318-25-4, A common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, molecular formula is C7H14ClNO3, 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.

The imidate salt 2g2(1.4g, 7.2mmol, 1 eq.) was combined with 2-(methylthio)-aniline 211 (0.96g, 7.50mmol, 1 eq.) in ethanol (15 mL) under an N2 atmosphere. Thereaction mixture was stirred at R.T. (1 h) and monitored by HPLC. The reactionmixture was concentrated and then ether was added and the mixture filtered. Thesolids were washed with ether and the combined ether washes concentrated in vacuo.The resulting adduct 2I2 was obtained as a yellow oil (1.66g, 82percent) and used as is in the next step. MS electrospray: (M + H)+; 282 and (M – H)-; 280.

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6520-83-8, 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. 6520-83-8, name is Ethyl 2-methoxy-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 12 5-(7-Methoxy-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid 2-Methoxy-6-methylbenzoic acid ethyl ester (500 mg, 2.67 mmol), N-bromosuccinimide (483.8 mg, 2.72 mmol) and 2,2′-azobis(2-methyl-propionitrile) (30.2 mg, 0.123 mmol) in carbon tetrachloride (10 ml) were heated to reflux. After 18 hours, the reaction mixture was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane (100 ml) and washed with water (2*50 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue (702 mg) was purified by column chromatography using a mixture of hexanes/dichloromethane (1:1) as eluent, which afforded 573 mg (85%) of 6-bromomethyl-2-methoxy-benzoic acid ethyl ester as an oil. 1H-NMR (CDCl3): delta7.37 (t, 1H, J=8.4 Hz), 7.01 (d, 1H, J=8.1 Hz), 6.90 (d, 1H, J=8.4 Hz), 4.54 (s, 2H), 4.45 (q, 2H, J=7.2 Hz), 3.82 (s, 3H), 1.42 (t, 3H, J=9 Hz).

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

Reference:
Patent; Novo Nordisk A/S; Ontogen Corporation; US6410556; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics