Tag: M.W=200-300

Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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. SDS of cas: 99548-54-6

[000576] Synthesis of 9: [000577] A mixture of 7 (228 mg, 1.0 mmol), 8 (288 mg, 1.4 mmol), Na2C03 (212 mg, 2 mmol) and Pd(PPh3)4 (115 mg, 0.10 mmol) in 2 mL of toluene, 2 mL of ethanol and 2 mL of water was stirred under N2 protection at 80 C for 17 hours concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1 : 50) to give 9 as white oil (260 mg, yield: 83.8%). LC-MS m/z: 311.1 [M+H]+. LC-MS Purity (214 nm): > 96%; tR = 2.256 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 99548-54-6, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; ERB, Michael; QI, Jun; (96 pag.)WO2016/196879; (2016); 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. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

A solution of sodium hydroxide (2.85 g, 71.3 mmol) in water (3 ml) was added to a stirred solution of diethyl oxaloacetate sodium salt (8.7 g, 50 mmol) in water (50 ml) and the mixture stirred for 20 minutes. Cyclopropylcarboxamidine hydrochloride salt (5.0 g, 40 mmol) was added to the solution and the mixture was heated at 70 0C overnight, then cooled to ambient temperature and acidified to pH1 by the cautious addition of concentrated hydrochloric acid. The precipitate was isolated by filtration and dried to yield 2-cyclopropyl-4-hydroxypyrimidine-6-carboxylic acid (4.7 g, 63%). 1H nmr (400MHz, d6-DMSO) deltaH 13.30 (1 H, br s), 12.97 (1 H, br s), 6.59 (1 H, s), 1.94 (1 H, quintet), 1.04 (4H, m) ppm.

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WHITTINGHAM, William, Guy; WINN, Caroline, Louise; GLITHRO, Harry; BOUSSEMGHOUNE, Mohamed, Abdelouahab; ASPINALL, Mary, Bernadette; WO2010/92339; (2010); A1;,
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Reference of 1459-96-7, 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. 1459-96-7 name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, 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.

Intermediate A51A: 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid To a solution of dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (0.92 g, 4.07 mmol) in MeOH (5 mL) was added LiOH (0.102 g, 4.27 mmol) in water (4 mL) at RT. The reaction mixture was heated at 65 C. for 6 h. It was then cooled to RT and concentrated. The residue was acidified with 1N HCl to pH ?2. The solid (presumed side product diacid) was removed by filtration. The filtrate was extracted with EtOAc, and the combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51A as a white solid, which was used for the next step without further purification. MS(ES): m/z=213 [M+H]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 12.11 (s, 1H), 3.66 (s, 3H), 1.78-1.58 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Electric Literature of 653-92-9,Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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: To a solution of (2) in 1 ,4-dioxane (4 mL) were added 1 ‘1 [bis(diphenylphosphino) ferrocene] dichloropalladium(ll) (0.2 eq), Na2C03 (8 eq) and one of the following regents heteroarylboronic acid or heteroaryiboronic acid pinacol ester or heteroarylboronic MIDA ester (2 eq) in a microwave tube. After addition of H20 (1 mL), the tube was sealed and the reaction mixture was stirred at 90C for 16 h. The mixture was allowed to cool to room temperature, was filtered through celite and MgS04 and the filter was repeatedly washed with ethyl acetate. After removing the solvent under reduced pressure, the crude residue was dissolved in saturated aqueous Na2C03 solution. The aqueous layer was extracted three times with CHCI3 and the combined organic layers were washed with saturated, aqueous NaCI solution and dried over Na2S04). The organic solvent was removed under reduced pressure and the residue was purified by preparative HPLC to obtain the appropriate target compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-fluorobenzoate, its application will become more common.

Reference:
Patent; FRIEDRICH-ALEXANDER-UNIVERSITAeT ERLANGEN-NUeRNBERG; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BANERJEE, Ashutosh; BARTUSCHAT, Amelie; EITEL, Katrin; GMEINER, Peter; HEINRICH, Markus; HOFMANN, Josefa; HUeBNER, Harald; RAMPP, Hannelore; SCHAAKE, Benjamin; KOBILKA, Brian; SUNAHARA, Roger; CLARK, Mary Joyce; FISH, Inbar; SHOICHET, Brian; (90 pag.)WO2019/110521; (2019); 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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 1-bromocyclobutanecarboxylate

A) Ethyl 1-azidocyclobutane-1 -carboxylate: To a flask was added ethyl 1-bromocyclobutane-1-carboxylate (5.0 g, 25 mmol), dimethylformamide (120 mL), and sodium azide (2.43 g, 37.5 mmol). After stirring at room temperature for 2 days, the reaction was taken up in ether and washed with water (3 x 150 mL). The organic layer was removed and dried over magnesium sulfate. The drying reagent was removed by vacuum filtration and the solvent removed by rotary evaporator to give a colorless liquid, 3.69 g, yield 87%. 1H-NMR (CDCl3) delta 1.29 (t, 3H), 2.00 (m, 2H), 2.25 (m, 2H), 2.55 (m, 2H), 4.22 (q, 2H); IR (neat) 2109 cm-1.

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

Reference:
Patent; Pfizer Products Inc.; EP952148; (1999); A1;,
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Related Products of 52727-57-8, These common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, 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 mixture of methyl 2-amino-5-bromobenzoate (2.32 g, 10.1 mmol), 4-fluorophenylboronic acid (1.70 g, 12.1 mmol, 1.20 equiv), PdCl2(amphos)2 (79.0 mg, 0.112mmol, 1.1 mol %), and tripotassium phosphate n-hydrate (3.28 g, ca. 12 mmol, ca. 1.2 equiv)were added 1,4-dioxane (40 mL) and H2O (4 mL) at room temperature and the mixture washeated at 100 C with stirring for 16 h. After cooling to room temperature, the mixture wasconcentrated under reduced pressure. The mixture was extracted with EtOAc (10 mL × 3),and the combined organic extract was washed with brine (5 mL), dried (Na2SO4), and, afterfiltration, the filtrate was concentrated under reduced pressure. The residue was purified byrecrystallization from n-hexane to give methyl 2-amino-5-(4-fluorophenyl)benzoate (2.01 g,8.20 mmol, 82.0%) as a pale yellow solid.

Statistics shows that Methyl 2-amino-5-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 52727-57-8.

Reference:
Article; Nakamura, Yu; Yoshida, Suguru; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 6; (2017); p. 858 – 861;,
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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. 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 57381-59-6

Compound 33b (24.00 g, 102.99 mmol) was dissolved in methanol (300 mL), and N,N-dimethylformamide (100 mL), triethylamine (100 mL), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (12.62g, 15.45 mmol) were added successively. The reaction mixture was stirred under a carbon monoxide atmosphere (50 psi) for 16 hr at 80 C, filtered, concentrated under reduced pressure to dryness, diluted with 100 mL of water, and extracted with ethyl acetate (500 mL×2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to dryness, and purified by silica gel column chromatography (petroleum ether/ethyl acetate=100-0%) to give Compound 33c (11.00 g). 1H NMR (400 MHz, CDCl3) delta3.95(s, 3H), 3.97(s, 3H), 7.20-7.24 (m, 1H), 8.21-8.23 (m, 1H), 8.63-8.65 (m, 1H). MS-ESI calculated value [M+ H]+ 213, measured value 213.

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

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; CHEN, Bin; YAO, Yuanshan; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (69 pag.)EP3489235; (2019); A1;,
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Application of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 solution of methyl 4-bromo-3-fluorobenzoate (526 mg, 2.26 mmol) in dioxane (10 mL) and H20 (2 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)- 1H-pyrazole- 1 -carboxylate (797 mg, 2.71 mmol), K3P04 (958 mg, 4.51 mmol) and XPhos-G2-Pd-preCat (35.5 mg, 0.045 mmol) at rt. The reaction was stirred under N2 at 60 C overnight. The reaction mixture was diluted with EtOAc,washed with H20 and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by normal phase chromatography to give two products as white solids. Intermediate 151A (463 mg, 64%): ?H NMR (400MHz, CDC13) oe 8.51 (d,J=1.5 Hz, 1H), 8.10 (s, 1H), 7.84 (dd,J=8.1, 1.5 Hz, 1H), 7.79 (dd, J=11.4, 1.5 Hz, 1H), 7.63 (t,J=7.8 Hz, 1H), 3.92 (s, 3H), 1.68 (s, 9H). LC-MS(ESI) m/z:321.0 [M+H]. Intermediate 151B (175 mg, 35%): ?H NMR (400MHz, CDC13)oe 8.06(d, J=1.8 Hz, 2H), 7.85 (dd,J=8.1, 1.8 Hz, 1H), 7.80 (dd,J11.7, 1.5 Hz, 1H), 7.66 (t,J7.7 Hz, 1H), 3.94 (s, 3H). LC-MS(ESI) m/z: 221.0 [M+H].

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); 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. 39622-80-5, name is Dimethyl 2-bromoisophthalate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39622-80-5

Diagram 2. Synthesis of Naproxen C0 (compound 9). Reactants and conditions: i/KMnO4 (2.0 equiv.), tBuOH/H2O (1/1), reflux, 4 hrs, then KMnO4 (2.0 equiv.), reflux, 16 hrs; ii/ MeOH, conc. H2SO4, reflux, 16 hrs; iii/ dimethyl 2-bromoisophthalate 6 (0.92 equiv.), Pd(PPh3)4 (0.03 equiv.), aq. Na2CO3 (4.2 equiv., 2 M), DME/EtOH, reflux, 16 hrs; iv/ aq. LiOH (7.2 equiv., 1 M), THF, reflux, 4 hrs.

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 39622-80-5.

Reference:
Patent; Institut National de la Recherche Agronimique; Slama Schwok, Anny; Delmas, Bernard; Quideau, Stephane; Bertrand, Helene; Tarus, Bogdan; US2014/163107; (2014); A1;,
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Electric Literature of 51760-21-5, The chemical industry reduces the impact on the environment during synthesis 51760-21-5, name is Dimethyl 5-bromoisophthalate, I believe this compound will play a more active role in future production and life.

C (3.3 g, 0.012 mol), bis(pinacolato)diboron (3.4 g, 0.013 mol), dried potassium acetate (3.6 g), [l,r-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl2, 0.2 g, 0.27 mol) were mixed in a 250 mL flask and evacuated for 1 hour before 100 mL dried, degassed l,4-dioxane was added. The reaction was stirred at 80 C under nitrogen atmosphere for 24 hours. After the reaction was completed, organic solvent was removed by rotovap and the remained solid was extracted with dichloromethane. The crude product was purified through a silica plug with a eluent of petroleum ether: ethyl acetate= 8: 1 to give pure D as a white solid (3.5 g, 90 % yield).

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

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LI, Jing; WANG, Hao; (162 pag.)WO2019/157013; (2019); A1;,
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