Tag: M.W=200-300

Reference of 1150566-27-0, 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 1150566-27-0 as follows.

(2R,4S)-4-Fluoro-2-[3-fluoro-5-(methylsulfanyl)phenyl]pyrrolidine hydrochloride (Preparation 25, 23.75 g, 89.4 mmol), KF (46.73 g, 804.3 mmol), ethyl 6- chloroimidazo[1 ,2-b]pyridazine-3-carboxylate (19.76 g, 87.6 mmol) were suspended in DMSO (350 ml). The reaction was heated at 130C for 82 h. The reaction mixture was allowed to cool to rt before being poured into distilled water (750 ml), which precipitated a beige solid. The liquid was decanted and the solid was washed with distilled water three times (3 x 250 ml). The beige solid was taken up in MTBE (500 ml) and partitioned between sat. aq. NH4CI (500 ml) and then finally brine (500 ml). The organic layer was dried (Na2S04), filtered and concentrated in vacuo to afford a dark reddish residue which was used without further purification (30.52 g, 82 %). LCMS m/z = 419 [M+H]+

According to the analysis of related databases, 1150566-27-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BENEVOLENTAI BIO LIMITED; BROWN, Alan; GLEN, Angela; (115 pag.)WO2020/39209; (2020); 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. 34812-95-8, name is Di-tert-butyl 2-methylmalonate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H22O4

[00129] To a salted ice (-10 – 0C) cooled solution of UB-12527 (20.0g, 86.8mmol, 1.0 equiv., in 190ml of dry tetrahydrofuran) 3.47g (86.8mmol, l.Oequiv., 60% in mineral oil) of sodium hydride was added. The mixture was warmed to room temperature then stirred for 30min. To the resulting white suspension 15.5ml (130mmol, 1.5equiv.) of 1,4- dibromobutane was added and the mixture was stirred overnight. The mixture was evaporated and the residue was dissolved in 250ml of water and 250ml of MTBE. The phases were separated, the organic was dried over sodium sulfate and evaporated. The crude product was purified by rectification (0.7-0.8mbar, 111-125C). Yield: 14.4g (39.5mmol, 45.5%) colourless, clear oil. GC: 96.7%.

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; APOSENSE LTD.; VAN GELDER, Joel M.; LEVY, Menashe; ARGOV, Mirit; BEN-AMI, Miri; ZIV, Ilan; WO2013/150534; (2013); A1;,
Ester – Wikipedia,
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Electric Literature of 106896-49-5, A common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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.

Example 1c Preparation of 3-Bromo-4-cyano-benzoic acid methyl ester A solution of 4-Amino-3-bromo-benzoic acid methyl ester (1.00 g, 4.35 mmol) in dichloromethane (20 mL) is cooled to -10 C. and treated dropwise with 90% tert-butyl nitrite (0.58 g, 0.67 mL, 5.08 mmol) followed by boron trifluoride diethyl etherate (0.94 g, 0.81 mL, 6.62 mmol). The suspension is allowed to warm to room temperature and stirred for 4 h. Diethyl ether (20 mL) is added, and the off-white solid is collected by filtration, washed with diethyl ether and dried briefly under high vacuum. The solid is then suspended in toluene (15 mL) and cooled to 0 C. A solution of copper (I) cyanide (0.52 g, 5.8 mmol) and sodium cyanide (0.71 g, 14.5 mmol) in water (10 mL) is added dropwise over 10 min. The mixture is stirred at 0 C. for 30 min, allowed to warm to room temperature, and then heated to 60 C. After 1 h, the solids are completely dissolved. The mixture is allowed to cool to room temperature, and ethyl acetate (20 mL) and water (20 mL) are added. The aqueous layer is separated and extracted with ethyl acetate (2*20 mL). The organic layers are combined, washed with water (2*10 mL) and brine, dried over Na2SO4, filtered and concentrated at reduced pressure. The solid residue obtained is recrystallized from hexanes/ethyl acetate to afford 3-Bromo-4-cyano-benzoic acid methyl ester (0.42 g, 39%) as a tan solid. The recrystallization mother liquor is concentrated and chromatographed (Biotage, 95:5 to 85:15 hexanes/ethyl acetate) to afford an additional portion of 3-Bromo-4-cyano-benzoic acid methyl ester (0.34 g, total yield: 0.76 g, 73%).

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; US2008/119457; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55954-23-9, 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. 55954-23-9, name is Methyl 2,4-dichlorophenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0198] To the mixture of methyl 2-(2,4-dichlorophenyl)acetate (0.5 g, 2.29 mmol) in THF (10 mL) was added NaH(0.12 g, 2.98 mmol) at oo C. portionwise, then the mixturewas stirred at 25 C. for 0.5 hr, then to the mixture was addedMel (0.42 g, 2.98 mmol) dropwise, the mixture was stirred at25 C. for 2 hrs. After the starting material was consumedcompletely detected by TLC, the mixture was quenched byH20 (lOmL), extracted withEtOAc (10mL*3). The organicswere dried over Na2S04 and concentrated in vacuum to getthe title compound (0.3 g, yield: 50.8%) as yellow oil.

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 2,4-dichlorophenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; (150 pag.)US2016/31892; (2016); 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. 98545-64-3, name is Methyl 4-amino-2-bromobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-amino-2-bromobenzoate

To a solution of 4-amino-2-bromobenzoic acid methyl ester (1700 mg, 7.368 mmol) in concentrated hydrochloric acid (27 mL) and water (102 mL) was added dropwise a solution of sodium nitrite (567 mg, 8.104 mmol) in water (25 mL) at -5C, and the mixture was stirred at -5C for 30 minutes. To the reaction mixture was added dropwise a solution prepared in (1-A) at -5C, the reaction temperature was gradually elevated, and the mixture was stirred at room temperature for 2 hours. The obtained viscous material was collected by filtration, the obtained viscous material was dissolved in chloroform, dried, and concentrated under reduced pressure. The obtained residue was purified by a silica gel column chromatography (hexane:ethyl acetate = 100:0?60:40) to give methyl 2-bromo-4-(chlorosulfonyl)benzoate (997 mg, 43%) as an orange solid. 1H-NMR (DMSO-d6) delta 3.86 (3H, s), 7.66 (1H, dd, J = 1.5 Hz, 7.9 Hz), 7.76 (1H, d, J = 7.9 Hz), 7.84 (1H, d, J = 1.5 Hz).

The synthetic route of 98545-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; KATO, Taku; SAKAMOTO, Toshiaki; KUBO, Akira; SAWAMOTO, Daisuke; EP2896613; (2015); 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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H13BrO2

Example 36E tert-butyl 5′-amino-2′-methyl[1,1′-biphenyl]-3-carboxylate A mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.00 g, 19.8 mmol) and tert-butyl 3-bromobenzoate (5.08 g, 19.8 mmol) in 1,4-dioxane (110 mL) and water (30 mL) was degassed under a N2 flow for 40 minutes. Potassium carbonate (13.7 g, 99 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (816 mg, 1.00 mmol) were added, and the mixture stirred at 80° C. for 7 hours. Water was then added to the reaction mixture, and it was extracted with ethyl acetate (2*). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using a Biotage® SNAP 340 g silica column, eluted with 10-25percent ethyl acetate in iso-hexane, to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.97-7.93 (m, 2H), 7.49-7.41 (m, 2H), 7.06 (d, J=8.0 Hz, 1H), 6.64 (dd, J=2.4, 8.0 Hz, 1H), 6.60 (d, J=2.4 Hz, 1H), 3.60 (broad s, 2H), 2.14 (s, 3H), 1.60 (s, 9H).

According to the analysis of related databases, 69038-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-bromo-4-fluorobenzoate

Example 38a Methyl 5,5′-difluoro-2′-nitrobiphenyl-2-carboxylate To 2-bromo-4-fluoro-1-nitrobenzene (185.16 mg, 0.842 mmol) was added Pd2dba3 (23.12 mg, 0.025 mmol) and copper powder (271 mg, 4.26 mmol). Dimethylsulfoxide (2.3 ml) and methyl 2-bromo-4-fluorobenzoate (0.122 ml, 0.842 mmol) were added and the mixture was stirred vigorously at 100 C. for 2 h. The mixture was cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered. The filtrate was washed with water and dried (anhydrous Na2SO4) and concentrated to give a yellow oil (279.8 mg). This oil was utilized without purification for the preparation of Example 38b.

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 653-92-9.

Reference:
Patent; AbbVie Inc.; Enanta Pharmaceuticals, Inc.; Ku, Yiyin; McDaniel, Keith F.; Chen, Hui-Ju; Shanley, Jason P.; Kempf, Dale J.; Grampovnik, David J.; Sun, Ying; Liu, Dong; Gai, Yonghua; Or, Yat Sun; Wagaw, Seble H.; Engstrom, Kenneth; Grieme, Tim; Sheikh, Ahmad; Mei, Jianzhang; (46 pag.)US9309279; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, 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 79669-50-4, Safety of methyl 5-bromo-2-methyl-benzoate

Step A Methyl 5-Bromo-alpha-(3-isopropylphenoxy)-o-toluate Treat a solution of 15 gm. (0.0655 mole) of methyl 5-bromo-o-toluate prepared according to Example 2 Step B in 75 ml. of carbon tetrachloride portionwise during 30 minutes with a mixture of 12.24 gm. (0.0688 mole) of N-bromosuccinimide and 130 mg. of benzoyl peroxide. Heat the resulting mixture at reflux for 3 hours. Cool to room temperature and separate the succinimide by filtration. Remove the solvent under vacuum to obtain methyl alpha,5-dibromo-o-toluate as a yellow residual oil.

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

Reference:
Patent; Merck & Co., Inc.; US4282365; (1981); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6279-86-3, name is Triethyl methanetricarboxylate, 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 6279-86-3, category: esters-buliding-blocks

To a solution of 1.00 mL of the alcohol (A-lOa) (1.00 equiv., 7.94 mmol) and 3.44 mL of triethyl methanetricarboxylate (2.00 equiv., 15.9 mmol) in 30.0 mL of anhydrous toluene at room temperature, 15.9 mL of 1M trimethyl phosphine solution in toluene (1M, 2.00 equiv., 15.9 mmol) was added. The resulting solution was cooled to -78C. DIAD (3.13 mL, 2.00 equiv., 15.9 mmol) was added slowly at such a rate to maintain the temperature of the reaction at -75C to -77C. The reaction was then stirred at -78C for 0.5 hours and warmed to room temperature for 1-3 hours and was allowed to run overnight. Solvent was concentrated in vacuo to get crude. The crude was purified by column chromatography using hexane and ethyl acetate to yield compound (A-lOb) as clear oil (2.46 g, 92.1 %). 1H NMR (600MHz, CHLOROFORM- d) d = 4.45-7.43 (d, 2H), 7.30-7.20 (m, 3H), 4.22-4.13 (m, 6H), 1.23-1.19 (t, =7.2Hz, 9H).

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; EPIODYNE, INC.; MEDINA, Julio Cesar; MCGEE, Larry; WEI, Zhi-Liang; SADLOWSKI, Corinne; SEIDL, Frederick; BHATT, Ulhas; WANG, Xiaodong; NGUYEN, Thomas; SPERANDIO, David; DING, Pingyu; NERURKAR, Alok; LI, Yihong; DUQUETTE, Jason; (307 pag.)WO2019/195634; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 126430-46-4, These common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, 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.

b) Preparation of 4-(N-Boc-L-valyloxy)butyric acid benzyl ester N-Boc-L-valine (1.3 g, 6 mmole) was dissolved in dioxane (5 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 3.8 ml, 6 mmole), and the solution was evaporated and coevaporated with toluene several times. The residue was dissolved in DMF (15 ml) and 4-bromobutyric acid benzyl ester (1.28 g, 5 mmole) was added to it. The reaction was kept for 18 hr, and then poured into sodium bicarbonate aqueous solution and extracted with dichloromethane. The organic phase was dried and the product was isolated with silica gel column chromatography, 1.2 g.

Statistics shows that Benzyl 4-bromobutanoate is playing an increasingly important role. we look forward to future research findings about 126430-46-4.

Reference:
Patent; AB, Medivir; US2002/128301; (2002); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics