Tag: M.W=200-300

Some common heterocyclic compound, 139102-34-4, name is Methyl 4-bromo-2-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. Application In Synthesis of Methyl 4-bromo-2-methoxybenzoate

Step 1: Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoateTo a 100 mL round-bottomed flask equipped with a stir bar was added methyl 4- bromo-2-methoxybenzoate (1.79 g, 7.30 mmol), 4,4,4?,4?,5 ,5 ,5?,5?-octamethyl-2,2?- bi(1,3,2-dioxaborolane) (2.78 g, 10.9 mmol), PdCl2(dppf) (0.267 g, 0.365 mmol), and potassium acetate (2.15 g, 21.9 mmol) at ambient temperature. The flask was sealed witha septum, dioxane (36.5 ml) was added, and the atmosphere was purged with N2 (g). The reaction was then heated to 90 C with stirring for 3 h and cooled to room temperature. The reaction was concentrated, the residue was dissolved in EtOAc and washed with 1 M aq. HC1 and sat. aq. NaC1. The organics were dried (Na2504), filtered, and concentrated. The residue was purified by silica gel column chromatography (Teledyne ISCOCombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep 5i02 80 g, loaded as DCM solution) to afford (methyl 2- methoxy-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoate (1 .87 g, 88 %) as a tan solid: ?H NMR (400 MHz, CDC13) oe 7.76 (d, J=7.7 Hz, 1 H), 7.42 (dd, J=7.7, 0.9 Hz, 1 H), 7.39 (s, 1 H), 3.96 (s, 3 H), 3.90 (s, 3 H), 1.36 (s, 12 H); HPLC: RT=1.284 mm(Waters Acquity BEH C,8 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1% TFA, 1.5 mill gradient, wavelength=254 nm); MS (ES): mlz= 293 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139102-34-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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Reference of 1014645-87-4, The chemical industry reduces the impact on the environment during synthesis 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, I believe this compound will play a more active role in future production and life.

A suspension of 2-(3-(3-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenoxy)azetidin-1-yl)-5-chloronicotinic acid (D110) (150 mg, 0.306 mmol), 1-Hydroxybenzotriazole hydrate (47 mg, 0.306 mmol) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (88 mg, 0.46 mmol) in dimethylformamide (2 ml) was stirred 40 min at room temperature. A solution of methyl 4-(1-aminocyclopropyl)benzoate (D7) (68.9 mg, 0.306 mmol) and triethylamine (0.042 ml, 0.306 mmol) in dimethylformamide (2 ml) was added and the resulting mixture was stirred 40 min at room temperature. Water (2 ml) was added and the resulting precipitate was collected by filtration and purified by Biotage column (10g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 80/20. Collected fractions, after solvent evaporation, afforded tert-butyl 4-(3-((1-(5-chloro-3-((1-(4-(methoxycarbonyl)phenyl)cyclopropyl)carbamoyl)pyridin-2-yl)azetidin-3-yl)oxy)phenyl)piperazine-1-carboxylate (135 mg)

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 4-(1-aminocyclopropyl)benzoate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
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Synthetic Route of 7686-78-4, The chemical industry reduces the impact on the environment during synthesis 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, I believe this compound will play a more active role in future production and life.

Preparation method: under an argon atmosphere, add 0.2 mmol of N-pyrimidine porphyrin compound, 0.36 mmol of ethylene cyclopropane compound to a 35 mL Shrek tube.0.008 mmol of [Cp*Rh(CH3CN)3](SbF6)2, 0.08 mmol of 1-adamantanic acid, 0.04 mmol of silver hexafluoroantimonate, methanol 0.5 mL, reacted at 90 C for 12 hours; after the reaction, using acetic acid Ethyl ester was rinsed, concentrated under reduced pressure, and then chromatographed on silica gel (200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio: 0/100 to 100/0). The yield was 81% and E/Z > 20:1.

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, Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengzhou University; Zhu Xinju; Wang Qiuling; Zhi Changlei; Li Jing; Liu Shuang; Zhao Xuemei; Hao Xinqi; Song Maoping; (15 pag.)CN109180648; (2019); A;,
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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. 107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Product Details of 107317-58-8

To a mixture of methyl 4-bromo-3-(trifluoromethyl)benzoate (1.00 g, 3.53 mmol), bis(pinacolato)diboron (1.79 g, 7.06 mmol), and KOAc (1.04 g, 10.6 mmol) in DMSO (15 mL) was added Pd(PPh3)4 (816 mg, 0.706 mmol) under N2 atmosphere. Then the mixture was heated to 120C for 3 hours. The reaction mixture was cooled followed by an aqueous/EtOAc workup to give the crude product (2.3 g) as a yellow oil.

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; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); 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 6279-86-3 as follows. Quality Control of Triethyl methanetricarboxylate

5-ethyl-6-{4-[(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-5(lH)-yl]phenyl}-4-hydroxy-2- oxo-l,2-dihydropyridine-3-carboxylic acid hydrochloride (1:1) (Cpd 246)Step 1:A solution of l-(4-chlorophenyl)butan-l-one (5.00 g, 27.37 mmol) and t-butyl amine(11.60 mL, 109.90 mmol) in DCM (30 mL) was cooled to 0 C. A solution of TiCl4 (1MDCM, 18.00 mL, 18.00 mmol) was added dropwise via syringe pump over 30 min. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with DCM (200 mL) and then the reaction was quenched with aHC03 (aqueous saturated, 60 mL). After vigorous shaking, the organic phase was separated using a PTFE phase separator, then dried over Na2S04. The solvent was removed to afford a colorless oil (5.30 g, 81), which was used directly in the next step without furtherpurification.The oil (2.14 g, 8.99 mmol) and triethylmethane tricarboxylate (2.20 mL, 10.46 mmol) in diglyme (9 mL) were heated at 160 C for 2 h. After the mixture was cooled to room temperature, a white solid was collected by filtration and washed with Et20. The resulting product (1.54 g, 53%) was obtained as a colorless crystalline material.XH NMR (500 MHz, DMSO-i?) delta ppm 0.95 (t, J=7.4 Hz, 3H) 1.30 (t, J=7.1 Hz, 3H) 2.18 (d, J=7.4 Hz, 2H) 4.34 (q, J=7.1 Hz, 2H) 7.44 (d, J=8.2 Hz, 2H) 7.57 (d, J=8.2 Hz, 2H) 11.43 (br. s., 1H) 13.57 (s, 1H). LC-MS 322.2/324.2 [M+H]+, RT 1.30 min.

According to the analysis of related databases, 6279-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33240; (2013); A1;,
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Application of 17100-65-1, 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. 17100-65-1 name is Methyl 2-bromo-4-methoxybenzoate, 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 stirred solution of 2-Bromo-4-methoxy-benzoic acid methyl ester (6) (2.5 g, 10.201 mmol) in DMF (15 mL) was degassed for 15 minutes with argon followed by the addition of Zn(CN)2 (2.39 g, 20.402 mmol) and Pd(PPh3)4 (1.17 g, 1.02 mmol) and the reaction mixture was stirred at 100C for 16 hours. The reaction mixture was diluted with Ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated. The crude was purified by column chromatography (silica, gradient: 20-30%) EtOAc in Hexane) to afford the Intermediate 7 (900 mg, 46%) as white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; THE BROAD INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION; INSTITUTO CARLOS SLIM DE LA SALUD; BURNS, Sean, M.; WAGNER, Bridget, K.; VETERE, Amedeo; (189 pag.)WO2018/175324; (2018); A1;,
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Electric Literature of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-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.

Step B: Methyl 3-amino-2-fluorobenzoate; In a 500 mL flask was placed 1,1-dimethylethyl carbamate (6.03 g, 51.5 mmol), methyl 3-bromo-2-fluorobenzoate (10 g, 42.9 mmol), Pd2(dba)3.CHCl3 (0.89 g, 0.86 mmol), xantphos (1.49 g, 2.57 mmol) and cesium carbonate (16.8 g, 51.5 mmol). The flask was sealed with a rubber septum, placed under high vacuum, and toluene (200 mL) was added. Three cycles of high vacuum/N2 were performed and the reaction mixture was stirred at 90 C. overnight. The reaction was filtered through a pad of celite with EtOAc washing and concentrated. To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h. The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over NaSO4, stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc:Hexane to give 5.53 g (76%) of the title compound of Step B. 1H-NMR (400 MHz, DMSO-d6) delta 6.92-7.01 (m, 3H), 5.37 (s, 2H), and 3.81 (s, 3H). MS (ESI): 170 [M+H]+.

The synthetic route of 206551-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 52727-57-8

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0 C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-white solid.

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; Universitat des Saarlandes; US2011/112067; (2011); A1;,
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Synthetic Route of 2876-78-0,Some common heterocyclic compound, 2876-78-0, name is Methyl 1-Naphthaleneacetate, molecular formula is C13H12O2, 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 1 potassium 1-(methoxycarbonylmethyl)-4-naphthalene sulfonate A solution of methyl 1-naphthaleneacetate (1 mL, 5.77 mmol) in carbon tetrachloride (1 mL) was cooled under nitrogen in an ice bath. Chlorosulfonic acid (0.38 mL, 5.7 mmol) was added dropwise over 8 minutes. After an additional 30 minutes, the viscous mixture was removed from the bath and was stirred at room temperature for 17 hours to give a white solid. The solid was partitioned between methylene chloride (5 mL) and water (5 mL). After filtering through solka-floc, the methylene chloride layer was extracted with more water (2*5 mL), and the combined aqueous extracts were basified with potassium carbonate to give a precipitate. The suspension was concentrated to approximately 5 mL and was cooled in an ice bath. The suspension was then filtered and the collected solid was washed with cold water (2 mL). The solid was dried under a stream of nitrogen to give the title compound as a white solid (0.84 g). 1H NMR (DMSO-d6, 500 MHz) delta 3.73 (s, OMe), 4.27 (s, CH2Ar), 7.53 (d, ArH), 7.71 (t, ArH), 7.76 (t, ArH), 8.06 (d, ArH), 8.10 (d, ArH) and 8.73 (d, ArH).

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

Reference:
Patent; Merck & Co., Inc.; US6271222; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 1000342-11-9, name is Methyl 3-amino-5-bromo-2-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 1000342-11-9, Recommanded Product: Methyl 3-amino-5-bromo-2-methylbenzoate

Step 1: Synthesis of tert-butyl 4-((5-bromo-3-(methoxycarbonyl)-2-methylphenyl)amino)piperidine-1-carboxylate To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (4.5 g, 18.44 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (11.01 g, 55.33 mmol) in dichloroethane (50 mL), acetic acid (6.64 g, 110.6 mmol) was added and reaction stirred at room temperature for 10 min. Then sodium triacetoxyborohydride (11.72 g, 55.28 mmol) was added at 0 C. and reaction stirred overnight at room temperature. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired compound (5.2 g, 66.24%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
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