Tag: M.W=200-300

Electric Literature of 29263-94-3, 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. 29263-94-3 name is Diethyl 2-bromo-2-methylmalonate, 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.

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

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

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Application of 17100-63-9,Some common heterocyclic compound, 17100-63-9, name is Methyl 4-bromo-3-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.

General procedure: A mixture of phenol (0.05 mol) (compounds 3, 8, 67, and 97-98), bromo-benzaldehyde (1.05 equiv.) (compounds 1-2, 9-12,48, 56, and 66), potassium carbonate (2 equiv.) and cupric oxide(0.3 equiv.) in pyridine (50 mL) was stirred under reflux for 12 h.The pyridine was distilled off in vacuo and the residue wasextracted with EtOAc (200 mL). The solution was concentrated andthe residue was purified by flash column chromatography (SiO2 orAl2O3), eluting with a hexane-DCM mixture, to yield the pureproduct as a solid in moderate yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromo-3-methoxybenzoate, its application will become more common.

Reference:
Article; Sun, Bin; Li, Lin; Hu, Qing-wen; Zheng, Hong-bo; Tang, Hui; Niu, Huan-min; Yuan, Hui-qing; Lou, Hong-xiang; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 186 – 208;,
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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. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H12O4

] the 23.0 NaH(1.2eq) and 600ml of anhydrous THF added into a 4L of reactor, cool down temperature to 0C, control the Temperature between 0 ~ 15 C then slowly dropping 100. 0 g of intermediate B of 300 mL THF solution and after the completion of addition the reaction was continued to stir for 0.5h ~ 1h.when the reaction was slowly cooled to -20 C ~ -15 C then slowly drop wise added 150mL THF solution of 62. 8 g (1. 1 eq.) 3-Bromo-1-propyne,agter the completion of addition slowly raise the temperature, at -20 C ~ -10 C the reaction was stirred for 1h, then at -10 C ~ 0 C the reaction was stirred for 2h and at 0 C ~ 10 C the reaction was stirred for 3h. The reaction was quenched with 400 mL of water and the intermediate C was extracted with ethyl acetate (400 mL X 2). The organic phase was washed with 200 mL of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated to dryness, stir beating with n-hexane, The filter cake was washed with a small amount of n-hexane to give a white solid C, Weight: 76. 4 g, yield: 64.5%, HPLC content: 95.3%

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 52787-14-1.

Reference:
Patent; SINOPHARM A THINK PHARMACEUTICAL CO LTD; (19 pag.)CN103739604; (2016); B;,
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Application of 33491-30-4, 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. 33491-30-4 name is 8-Bromo-2H-chromen-2-one, 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.

(3) Weigh 1.8g of Br-C8 (8.89mmol),0.28 g of Pd(PPh3)4 (0.24 mmol) in a SCHLENK reaction tube under N2 atmosphere,35 mL of toluene was added, and 3.53 g of tri-n-butyl 2-pyridinium (9.60 mmol) was added dropwise.The reaction was stirred at 110 C for 16 h. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure.It was separated and purified by silica gel column chromatography, and the mobile phase was dichloromethane.Finally, L-C8 was obtained as a white solid 1.49 g, and the yield was 83.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Xi’an Jiaotong University; Zhou Guijiang; Feng Zhao; Yang Xiaolong; (40 pag.)CN109608502; (2019); A;,
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These common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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. Quality Control of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate

Methyl 2-(4-bromophenyl)-2-methylpropanoate (689 mg, 2.68 mmol),(R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (630 mg, 2.61 mmol),Pd2(dba)3 (180 mg, 0.19 mmol),2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (550 mg, 1.26 mmol),Cs2CO3 (173 mg, 0.53 mmol) and1,4-dioxane (25mL)Add to a 50mL two-neck bottle,The reaction mixture was reacted under nitrogen for 12 h at 90 C.After the reaction was completed, the reaction was cooled to EtOAc. Add EtOAc (75 mL) and water to the filtrate(50 mL), the resulting mixture was shaken and layered. The aqueous phase was extracted with EtOAc (50 mL).Filtration and concentrating the filtrate under reduced pressure, and the obtained residue was purified by silica gel column chromatography (PE/EA (V/V)=1.2/1)The product was a white solid (200mg, 17.88%)

The synthetic route of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ·geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
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Synthetic Route of 139102-34-4, 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 139102-34-4 as follows.

[00197] Step 1: A mixture of methyl 4-bromo-2-methoxybenzoate (2.66 g, 10.85 mmol), 28% ammonium hydroxide (25 mL, 642 mmol) and ammonium chloride (2.0 g, 37.4 mmol) was stirred at RT for 20 min and then at 50 0C. Once the material converted forms to an oil (ca. 20 min), the mixture was cooled to RT and more ammonium hydroxide (25 mL, 642 mmol) and ammonium chloride (2.0 g, 37.4 mmol) were added. Upon completion of addition, the reaction mixture was stirred at RT overnight. After this time, the mixture was heated to reflux in an open flask to drive off the excess ammonia and then cooled to RT. The mixture was neutralized with cone. HCl and then extracted with ethyl acetate. The extract was dried (Na2SO4) and then concentrated to give a residue. The residue was purified by flash chromatography (40 g silica gel cartridge; EtO Ac/Hex) to give 4-bromo-2- methoxybenzamide (510 mg, 2.22 mmol, 20 % yield) as a white solid.

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARTER, Percy H.; CORNELIUS, Lyndon A., M.; WO2008/42925; (2008); A1;,
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Reference of 26218-04-2,Some common heterocyclic compound, 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, molecular formula is C15H23NO2, 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 mixture of 2, 4-dichloro-6- (l-methyl-lH-pyrazol-5- yl) -1, 3, 5-triazine (0.23 g, 1 mmol) , 2-ethylhexyl 4- aminobenzoate (0.50 g, 2 mmol) and potassium carbonate(0.30 g, 2.17 mmol) in dioxane (15 mL) is heated to 900C for 4 hours following the reaction by TLC. The solvent is evaporated at low pressure, the residue is diluted in methylene chloride and the organic phase is washed with water. The solvent is removed at low pressure and the resulting crude product is purified by silica gel chromatography to yield 2, 4-bis{4- [ (2- ethylhexyloxy) carbonyl]phenylamino}-6- (1-methyl-lH- pyrazol-5-yl) -1, 3, 5-triazine (0.56 g, 0.85 mmol, 85%, thick oil) .1H RMN (300 MHz, DMSO-d6) : delta 0.82-0.94 (m, 12H), 1.23- 1.46 (m, 16H), 1.67 (m, 2H), 4.17 (d, J= 4.4 Hz, 4H), 4.30 (s, 3H), 7.06 (br s, IH), 7.54 (d, J= 1.9 Hz, IH), 7.94 (br s, 8H), 10.29 (br s, 2H) .UV lambdamax= 293 nm epsilon= 59000 M’1 cm”1 (methanol) .

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

Reference:
Patent; ISDIN, S.A.; WO2006/64366; (2006); A1;,
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107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, 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. category: esters-buliding-blocks

General procedure: A suspension of 4-(((lS,4S,5R)-2-azabicyclo[2.2.1]heptan-5-yoxy)methy)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole hydroiodide salt l2dd (0.52 mrnol, 1 equiv.),methyl4-bromo-2/3-substituted benzoate 106-y (0 68 mmol, 1.3 equiv.), Cs2C03 (1.3 mmol,15 2.5 equiv.), Pd?(dha)3 (0.15 equiv.), BINAP (0.2 equiv.) in Toluene (10.0 mL) was heatedunder a nitrogen atmosphere at 1 J 0C for 16 h. The reaction rnixture was cooled to roomtemperature, diluted with ethyl acetate and filtered through a pad ofCelite. The organic layerwas washed with brine, dried over anhydrous Na2S04, filtered and concentrated 1..mderreduced pressure. The crude material v.·as purified on ISCO silica gel column20 chromatography using hexane/ethyl acetate as eluents to give the desired methyl ester l06zwhich was used as such in the next step.

The synthetic route of 107317-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
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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Adding a certain compound to certain chemical reactions, such as: 87808-49-9, name is Methyl 2-bromo-4-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 87808-49-9, HPLC of Formula: C9H9BrO2

Methyl 2-bromo-4-methylbenzoate (0.0573 g, 0.25 mmol), alpha-methylstyrene (0.065 mL, 0.50 mmol), palladium acetate (0.0056 g, 0.025 mmol),Tris(4-trifluoromethylphenyl)phosphine (0.0233 g, 0.05 mmol), silver carbonate (0.1379 g, 0.5 mmol), p-toluenesulfonic acid monohydrate (0.0048 g, 0.025 mmol), 1,1,1,3 3,3-Hexafluoro-2-propanol (0.5 mL), o-xylene (0.5 mL), stirred uniformly in a clean and dry closed reaction tube, and then heated to 130 C for 12 hours.After completion of the reaction, the reaction tube was cooled to room temperature, and the reaction system was diluted with 30 mL of ethyl acetate and transferred to a 100 mL separatory funnel. 20 mL of a saturated aqueous solution of ammonium chloride was added thereto, shaken, and allowed to stand to remove the aqueous phase of the lower layer. After that, 20 mL of saturated brine was added thereto, and the mixture was shaken, and the mixture was allowed to stand. The lower aqueous layer was removed, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated. =20:1-10:1, v/v) Separate and purify, remove the solvent by rotary distillation, and drain the oil to obtain a colorless oil.The target product was 56.6 mg, yield 90%.

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; Shanxi University; Wen Zhenkang; Ge Xiaomin; Liu Yufang; Chao Jianbin; (16 pag.)CN108774206; (2018); A;,
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Synthetic Route of 6232-12-8, 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. 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 178 ethyl 5-{[({4-[(ethyloxy)carbonyl]phenyl}methyl)amino]carbonyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (2089) (2090) To a mixture of 2-[(ethyloxy)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid (600 mg, 2.24 mmol) obtained in Reference Example 176 and THP (6 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) and DMF (0.0500 mL, 0.650 mmol) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. To a suspension of the concentrated residue in THF (6 mL) were added ethyl 4-(aminomethyl)benzoate hydrochloride (966 mg, 4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol), and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure and ethyl acetate was added to the obtained residue. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was crystallized from ethyl acetate to give the title compound as a white powder (771 mg, 80%). (2091) melting point: 227-228 C. (2092) 1H NMR (300 MHz, DMSO-d6) delta 1.31 (3H, t, J=6.2 Hz), 1.36 (3H, t, J=6.2 Hz), 4.31 (2H, q, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz), 4.65 (2H, d, J=5.5 Hz), 7.50 (2H, d, J=8.5 Hz), 7.93 (2H, d, J=8.5 Hz), 8.57 (1H, s), 11.27 (1H, s), 13.53 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
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