Tag: M.W=200-300

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. 90971-88-3, name is Methyl 2-bromo-5-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 2-bromo-5-methylbenzoate

Example 15; Synthesis of 5-methyl-2-triisopropylsilanylsulfanyl-benzoic acid methyl ester (Method 15.) 2-Bromo-5-methyl-benzoic acid methyl ester (2.06 g, 9.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), triisopropylsilanethiol (1.37g, 7.2 mmol) and dry toluene (10 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 150 C. for 30 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (2:8). This furnishes the title compound as an oil, which is used in the next step without further purification.

The synthetic route of 90971-88-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kehler, Jan; Juhl, Karsten; Norgaard, Morten Bang; US2006/287386; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 59247-47-1,Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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 round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1 ,2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.l]heptane ll3h (150 rng, 0.42 mmol, l.O equiv.), Tol (20 rnL),tert-butyl4-bromobenzoate (161.2 mg, 0.63 mmoL 1.50 equiv.), Cs2C03 (408 8 mg, 1.25mmol, 3.0 equiv.), BIANP (13 mg), and Pd2(dha)3 (19 mg, 0.02 mmol, 0.05 equiv.). The5 resulting mixture was stirred at 110 °C overnight Solids were filtered out. l11e illtrate wasconcentrated under vacuum to a residue which was pmified by silica gel columnchromatography eluting with ethyl acetate/petroleum ether (l: 10 to 1 :5). Removal of solventsgave tert-huty 1 4-l(l S,4S,5R)-5-U 3-(2-chloro-6-methy lpheny 1)-5-cyclopropy 1-1,2-oxazol-4-y l] rnethoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]henzoate ll4a (l 00 mg, 45percent) as a light yellow10 oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, 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 185312-82-7, COA of Formula: C8H6BrClO2

Reference Example 12 4-bromo-2-chlorobenzyl alcohol Methyl 4-bromo-2-chlorobenzoate (477 g) of Reference Example 11 was dissolved in a mixed solution of ethanol (3000 mL) and water (680 mL), calcium chloride (212.2 g) was added at 10C, and the mixture was stirred for 30 min. To the solution was added sodium borohydride (144.7 g) by portions so that the inside temperature would not exceed 25C, and the mixture was stirred at room temperature for 5 hr. 1M Hydrochloric acid (5100 mL) was added dropwise to the reaction mixture, and the reaction solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue. After partitioning and extraction, the organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (399 g) as white crystals. 1H-NMR(CDCl3)delta(ppm):1.87(1H, t, J=5.8Hz), 4.74(2H, d, J=5.8Hz), 7.38(1H, d, J=8.2Hz), 7.42(1H, dd, J=1.8, 8.2Hz), 7.53(1H, d, J=1.8Hz).

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; Mitsubishi Tanabe Pharma Corporation; EP2017257; (2009); 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. 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate

A solution of dimethyl bicyclo [2.2.1] heptane-1, 4-dicarboxylate (500 mg, 2.356 mmol) and LiOH (169 mg, 7.07 mmol) in water (20 mL) and MeOH (10 mL) was stirred at RT for 48 hours. The solution was poured into 1 N HCl and extracted with EtOAc. The combined organic was dried over Na2SO4and concentrated in vacuo to give crude title compound.

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 110661-91-1, 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. 110661-91-1, name is tert-Butyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate (20 g, 53 mmol) in DMF (100 mL) at 0 C. was added KOtBu (7.73 g, 69 mmol). The mixture was stirred at 0 C. for 45 minutes, then tert.-butyl 4-bromobutanoate (15.4 g, 69 mmol) was added at 0 C. The reaction mixture was allowed to warm to room temperature and stir overnight. The mixture was portioned between ether and saturated aqueous NH4Cl. The organic solution was washed with water and saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The residue was taken into hot cyclohexane. The mixture was allowed to stand for 72 hours. The solvent was decanted and the residue was washed with cold cyclohexane. The solid was then dried under high vacuum to yield 4-(3-tert.-butoxycarbonyl-propoxy)-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-1a: 20.8 g). 1H NMR (400 MHz, CHLOROFORM-D) ppm 1.4 (s, 9H), 1.4 (t, J=7.1 Hz, 3H), 1.9 (m, 2H), 2.3 (t, J=7.5 Hz, 2H), 4.0 (t, J=5.9 Hz, 2H), 4.4 (q, J=7.1 Hz, 2H), 7.2 (m, 2H), 7.2 (m, 2H), 7.4 (m, 3H), 7.5 (m, 1H); m/z=519.0 (M+1).

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

Reference:
Patent; Pfizer Inc; US2006/241100; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 150529-73-0, The chemical industry reduces the impact on the environment during synthesis 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, I believe this compound will play a more active role in future production and life.

Step 2: [00153] To a solution of the ester (6.0 g, 26.2 mmol) in tert-butanol (24 ml_) was added, under nitrogen atmosphere, sodium iodide (7.8 g, 52.4 mmol), N1N’- dimethylethylenediamine (0.3 ml_, 2.6 mmol) and copper iodide (0.3 g, 1.3 mmol). The reaction mixture was heated in a microwave apparatus at 145C for 1 h. Water (100 mL) was added and the product was extracted with ethyl acetate (3 x 50 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel with a mixture of hexanes/ethyl acetate (8:2). This gave 3- iodophenylacetic acid methyl ester as a colorless oil (6.6 g, 86%). 1H NMR (400 MHz, CDCI3): d = 7.63 (m, 1 H), 7.58-7.61 (m, 1 H)1 7.23-7.26 (m, 1 H)1 7.05 (dd, J = 7.8 Hz, 1 H), 3.69 (s, 3H), 3.56 (s, 2H); LRMS (ESI): m/z = 277 (MH+).

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 2-(3-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROMETIC BIOSCIENCES INC.; ZACHARIE, Boulos; PENNEY, Christopher; GAGNON, Lyne; BIENVENU, Jean-Francois; PERRON, Valerie; GROUIX, Brigitte; WO2010/127440; (2010); 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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H19BrO2

1h: Preparation of Compound 8 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 5 g (1 equivalent) of 4-hydroxybenzonitrile, absolute ethanol 150 mL, and 15.7 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 8-bromooctanoate (10.5 g, 1 equivalent) was then added dropwise over 10 minutes. The resulting mixture was heated to reflux (75 C.) for 72 hours. The reaction mixture was cooled and the solids filtered off. The solvent was removed on a rotary evaporator. The crude residue was dissolved in methylene chloride (200 mL) and washed with saturated NaHCO3 (2*75 mL), H2O (1*100 mL) and brine (1*100 mL). The crude material was then dissolved in ethanol (125 mL) and water (10 mL). LiOH (5 g) was added and the resulting mixture was heated to reflux (75 C.) for 1 hour then stirred at ambient temperature overnight. The solvent was evaporated and 75 mL of H2O was added. The aqueous solution was acidified to a pH of about 3 with concentrated HCl and the flask cooled to 4 C. An off-white colored solid precipitated. This material was collected by vacuum filtration and dried on the high vacuum overnight to give the crude acid. These solids were further purified by recrystallization from Ethyl acetate/hexanes (95/5) and again with chloroform to give 4.5 g of the product, 8-(4-cyanophenoxy)octanoic acid (41% yield). Melting point: 137-140 C. Molecular Formula: C15H19NO3. Combustion analysis: %C: 68.94 (calc’d), 68.57 (found); %H: 7.33(calc’d), 7.13(found); %N: 5.36 (calc’d), 5.28 (found).

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 75567-84-9, A common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, molecular formula is C10H11BrO2, 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 flask were added compound 50-6 (1.0 g, 3.5 mmol, the mixture of two trans isomers) , methyl 3- (4-bromophenyl) propionate (1.3 g, 5.3 mmol) , palladium acetate (100 mg, 0.445 mmol) , t-BuXPhos (300 mg, 0.63 mmol) , cesium carbonate (2.0 g, 6.1 mmol) and 1, 4-dioxane (10 mL) , the mixture was stirred at 90 for 3 hours and concentrated. The obtained residue was purified by silica gel column chromatography (PE/EA (V/V) = 1/1) to give the title compound as a white solid (1.0 g, 64%) . MS (ESI, pos. ion) m/z: 470.2 [M+Na] +.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

541-16-2, name is Di-tert-Butyl malonate, 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 C11H20O4

Di-tert-butyl malonate (33.5 mL, 150 mmol) was added dropwise to a stirred suspension of NaH (6.0 g, 60 % suspension in oil, 150 mmol) in 1,2-dimethoxyethane (100 mL) under Ar, cooled in a water-ice bath. After stirring for 10 min, Intermediate 1G (16.2 g, 50 mmol) was added and the reaction was heated at 85 C for 20 h. After this time, acetic acid (100 mL) was added, the reaction flask was fitted with a distillation head and the temperature was raised to 130 C. 1,2-dimethoxyethane was distilled off under atmospheric pressure until the distillate was acidic (-100 mL). The distillation head was removed, a reflux condenser was attached, water (20 mL) was added and the reaction heated at 130 C for 12 h. The reaction was concentrated under reduced pressure and poured onto 200 g of ice and 100 mL of saturated aqueous NaOAc. Intermediate 1H was isolated as a white solid by filtration and further dried by reflxing with toluene in a Dean- Stark apparatus (11.0 g, 76 %). m/z ( +H)+= 288.2.1H- MR (400 MHz; DMSO-d6): delta 12.05 (bs, 1H), 8.79 (d, J= 4.5 Hz, 1H), 8.06 (dd, J= 9.2, 5.8 Hz, 1H), 7.94 (dd, J= 11.0, 2.8 Hz, 1H), 7.66-7.61 (m, 1H), 7.50 (d, J= 4.6 Hz, 1H), 2.41 (d, J= 7.6 Hz, 2H), 2.28- 2.23 (m, 1H), 1.87-1.78 (m, 2H), 1.73-1.64 (m, 6H).

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; SHAN, Weifang; WILLIAMS, David K.; ZHANG, Liping; (87 pag.)WO2019/74822; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 21597-54-6, name is Methyl 3-amino-2-naphthoate, 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 21597-54-6, Product Details of 21597-54-6

Mix 5.0g (11.8mmol)12-bromo-10,10-dimethyl-10hydro-indeno[1,2-b]triphenylene(12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene), 2.6 g (13.0 mmol) methyl 3-amino-2-naphthoate(methyl 3-amino-2-naphthoate),.13g (0.59 mmol) Pd(OAc)2, 0.17 g (0.59 mmol)Tri-tert-butylphosphonium tetrafluoroborate, 3.9 g (17.7 mmol) sodium tert-butoxide,80 ml of toluene was degassed and placed under nitrogen and then heated at 110 C for 16 h.After the reaction was completed, the mixture was allowed to cool to room temperature.The organic layer was extracted with dichloromethane and water and dried over anhydrous MgSO4.The solvent was removed and purified by silica gel column chromatography.The product was obtained (3.2 g, yield: 51%).

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

Reference:
Patent; Jiguang Technology Co., Ltd.; Yan Fengwen; Deng Jinming; Zhuang Lijie; (80 pag.)CN107629068; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics