Category: esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, 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 106896-49-5, category: esters-buliding-blocks

To a 250 rnL rmmd bottom flask purged with and maintained under Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Reference of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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 solution of ethyl 3-(dimethylamino)acrylate (4.33 mL, 30.3 mmol) and triethylamine (2.446 mL, 17.55 mmol) in Et2O (46 mL) was added dropwise to a solution of (Z)-2-chloro-N-hydroxybenzimidoyl chloride (2.3 g, 12.10 mmol) in Et2O (46.0 mL) to give a white suspension which was stirred overnight at 20 C. After 19 h, the salts were filtered and then rinsed with Et2O (30 mL). The filtrate was concentrated to dryness to give 5.86 g of an orange liquid which was purified by flash chromatography using a mixture of hexane/Et2O to afford ethyl 3-(2-chlorophenyl)isoxazole-4-carboxylate 3a (2.36 g, 77% yield) as a colorless oil; 1H NMR (DMSO-d6) was consistent with the desired product; MS m/z 252.1 (MH+); HPLC 100%, Rt=1.96 min, column 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(dimethylamino)acrylate, its application will become more common.

Reference:
Patent; Lamarre, Daniel; US2015/133495; (2015); A1;,
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Reference of 5335-05-7, The chemical industry reduces the impact on the environment during synthesis 5335-05-7, name is Chloromethyl benzoate, I believe this compound will play a more active role in future production and life.

A similar procedure [23] and [26] to that previously described for the preparation of 2 was followed using chloromethyl benzoate (45) (106 mg, 0.76 mmol) in acetone (0.2 mL), sodium iodide (339 mg, 2.28 mmol) in acetone (2.5 mL), and the mixture stirred at room temperature for 30 min. The solvent was removed in vacuo and the residue taken up in acetonitrile (1.5 mL). A solution of 1 (200 mg, 0.38 mmol) in acetonitrile (2 mL) was added and the mixture stirred at 80 C for 16 h. The solvent was removed in vacuo with purification by flash chromatography (dichloromethane/methanol 20:1) affording 3 as a yellow solid (110 mg, 0.14 mmol, 37%). mp 165-169 C; numax(NaCl)/cm-1 1087 and 1261 (C-O ester), 1697 (CO imide), 1733 (CO ester); m/z (FAB+) 660 (M+, 100%); (Found: M+ 660.2490, C42H34N3O5 requires 660.2498).

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, Chloromethyl benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rennison, David; Laita, Olivia; Bova, Sergio; Cavalli, Maurizio; Hopkins, Brian; Linthicum, Darwin S.; Brimble, Margaret A.; Bioorganic and Medicinal Chemistry; vol. 20; 13; (2012); p. 3997 – 4011;,
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Application of 14273-90-6,Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, 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: Typical procedure: Under a dry argon atmosphere, a solution of imidazole (Im, 2.05g, 30.1mmol) in dry THF (10mL) was added dropwise to stirred potassium tert-butoxide (3.36g, 29.9mmol) in dry THF (40mL) at 0C. The resulting reaction mixture was stirred for 2h, a solution of 5a (5.46g, 30.2mmol) in dry THF (10mL) was added dropwise. After refluxing the resulting mixture for 16h, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. After dissolving the residual liquid in dichloromethane, this solution was washed with water and brine several times, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an Rf value of 0.45 was collected and dried under reduced pressure to afford 1-[3-(methoxycarbonyl)propyl]imidazole

The synthetic route of 14273-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ichikawa, Tsukasa; Wako, Tsuyoshi; Nemoto, Nobukatsu; Reactive and functional polymers; vol. 99; (2016); p. 1 – 8;,
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Related Products of 42122-44-1, A common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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.

To a cooled solution (0 C, ice bath) containing 3-(3-(N-(2-(tert- butyldimethylsilyloxy)ethyl)methylsulfonamido)pyridin-4-yl)-N-(2-phenylpropan-2- yl)benzamide (0.090 g, 0.12 mmol) and dichloromethane (2 mL) was added O- (mesitylsulfonyl)hydroxylamine (0.080 g, 0.37 mmol) in dichloromethane (2 mL) quickly, dropwise. The solution was maintained at 0 C for 15 min, removed from the cooling bath and maintained at ambient temperature for 2 h. The solution was concentrated, dissolved in methanol (5 mL) and re-concentrated to afford l-amino-3- ( -(2-hydroxyethyl)methylsulfonamido)-4-(3-(2-phenylpropan-2- ylcarbamoyl)phenyl) pyridinium 2,4,6-trimethylbenzenesulfonate as a light yellow foam (470, MH+). The product thus obtained was dissolved in DMF (2.4 mL) and added slowly dropwise over 20 min to a cooled mixture (0C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethylacetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-( -(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[l,5-a]pyridine-3-carboxylate as a yellow residue. 1H NMR (500 MHz,CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J=7.93 Hz, 1 H), 7.77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H), 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H), 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=12.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters- Sunfire, 5u, CI 8, 4.6 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

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; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S.; WO2011/112186; (2011); A1;,
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344-14-9, name is Dimethyl 2-fluoromalonate, 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 C5H7FO4

Intermediate 345 A: Methyl 2-fluoropent-4-ynoate In a 20 mL microwave vial, a mixture of dimethyl 2-fluoromalonate (900 mg, 6.0 mmol) in DMA (5 mL) at room temperature with stirring, was treated with the slow addition of sodium hydride (240 mg, 6 mmol, 60%) at 0 C. The mixture was stirred for 10 minutes, then added 3-bromoprop-l-yne (743 mg, 5.0 mmol, 80% in xylenes) and the mixture was stirred vigorously at 25 C for 1.5 hours. TLC shows consumption of the bromide. A syringe needle was placed through the septum to allow gases to vent, then the mixture was heated at 90 C for 20 hours. The reaction was quenched with the careful addition under nitrogen of saturated NH4CI solution (0.5 mL), and extracted with ethyl acetate (3 X 25 mL). The combined extracts were dried over Na2S04 to give a few ml of a brown oil as crude product. The crude product was dissolved in ethyl acetate and rinsed 3 times with 10% LiCl to remove DMA. The organic layer was dried over sodium sulfate, and then concentrated to give an amber oil which was purified over silica gel in 9: 1 to 3 : 1 hexanes/EtOAc to afford methyl 2-fluoropent-4-ynoate (600 mg, 69% yield). NMR (400MHz, CHLOROFORM-d) delta 3.84 (s, 3H), 2.92-2.74 (m, 2H), 2.14-2.00 (m, 1H), 1.27 (d, J=5.3 Hz, 1H). LCMS 130.2 (M+H)+.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, 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 7686-78-4, Product Details of 7686-78-4

Preparation method: In air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.24 mmol of ethylene cyclopropane compound,0.003 mmol of [Ru (p-cymene) Cl2] 2, 0.06 mmol of 1-adamantanic acid,0.04 mmol of silver hexafluoroantimonate,Microwave at 50 C for 2 hours;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0)Dried to a pale yellow oil,The yield was 76% and E / Z> 20: 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); A;,
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Application of 35450-36-3,Some common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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.

Under an argon atmosphere, a solution of 125.1 g of 2-bromo-5-methoxybenzoic acid methyl ester (1) in tetrahydrofuran (216 mL) was added to 1160 mL of a tetrahydrofuran solution of methylmagnesium bromide (1.1 mol / L) at 1 to 11 C. Was added dropwise over 1 hour 45 minutes.The ice water bath was removed and stirred at room temperature (~ 25 C.) for 19.5 hours.The reaction solution was added dropwise to an ammonium chloride aqueous solution (NH 4 Cl 200 g / H 2 0 800 g) at 5 to 23 C. over 5 minutes,1000 g of toluene was added and the mixture was separated into an organic layer and an aqueous layer.After washing the organic layer with 1000 g of water, it was separated into an organic layer and an aqueous layer, and the organic layer was concentrated under reduced pressure.250 mL of a mixed solution of ethyl acetate-heptane (1/9, v / v) was added to 136 g of the obtained crude product, and the mixture was stirred at 22 to 25 C. for 16 hours.The resulting slurry was filtered with suction and washed with 125 mL of a mixed solution of ethyl acetate-heptane (1/9, v / v).The obtained solid was dried under reduced pressure (40 C., 1 hour 15 minutes)To obtain 90.6 g (yield 72.4%) of white solid 2- (2-bromo-5-methoxyphenyl) propan-2-ol (2).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; Shirokawa, Shinichi; Shibata, Tsuyoshi; Kimura, Yoshihiro; Oi, Takahiro; Tanimoto, Toshihide; Wada, Hisaya; (42 pag.)JP2017/105748; (2017); A;,
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Synthetic Route of 115118-68-8,Some common heterocyclic compound, 115118-68-8, name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, molecular formula is C14H24O6, 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.

Intermediates Ia and Ib are prepared by the methods described in literatures. Dissolve 15 g of intermediate Ibin 200 mL of ethanol, add 30 mL of NaOH (12 g, 0.3mol) aqueous solution, reflux the reaction solution for 3 hours, filterit in vacuum to obtain white solid and wash it with ethanol for 3 times to obtain intermediate Ic.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; Southeast University; GOU, Shaohua; EP2913335; (2015); A1;,
Ester – Wikipedia,
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Reference of 583-02-8, 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. 583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,2,6,6-tetramethylpiperidine (TMPH, 1.5equiv) in THF (2mL/mmol of ester), a solution of n-butyllithium (1.45M in hexane, 1.5equiv) was added at -30C over 30min. After cooling at -78C, tris(isopropyl)borate (2.0equiv) was added over 20min. Ethyl benzoate or 4-(trifluoromethyl)benzoate or ethyl isonicotinate (1.0equiv) was added via syringe to the reaction mixture over 10min and the mixture was stirred at -78C for 3.5h. After warming to -30C, glacial acetic acid (1.5equiv) was added causing the internal temperature rising to -10C. Neopentyl glycol (1.5equiv) was added and the mixture was stirred at room temperature for 2h. Dichloromethane (20mL/mmol of ester) was then added. The organic phase was successively washed three times with satd aqueous NH4Cl, with satd aqueous NaHCO3 and with water, dried over MgSO4 and evaporated to give the desired compounds.

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, Ethyl 4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
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Ester – an overview | ScienceDirect Topics