Tag: M.W=200-300

Related Products of 40876-98-0, 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 40876-98-0 as follows.

Sten 1: Synthesis of ethyl 1 -(2-fluorobenzyl)-5 -hydroxy- 1 H-pyrazole-3 -carboxylate.A mixture containing acetic acid (15 equiv.) and diethyl oxalacetate sodium salt (1 equiv.) in benzene was stirred at 25 C for 30 mm. To this mixture was added (2-fluorobenzyl)hydrazine hydrochloride (2 equiv.). The resulting mixture was heated to 100 C for 2 h. The mixture was cooled to 23 C and concentrated under vacuum. The precipitate formed was collected by filtration. The solid was dissolved in ethyl acetate and washed with iN HC1 solution (x3). The organic layer was dried, filtered, and evaporated to give a solid containing the desired product. The solid was rinsed with a minimal amount of a methanol-diethyl ether mixture, dried under vacuum to deliver the desired intermediate, ethyl 1 -(2-fluorobenzyl)-5 -hydroxy-1H-pyrazole-3-carboxylate (11.8 g, 71 % yield) as a cream colored solid.?H NMR (500 MHz, CD3OD) ppm 7.24 – 7.41 (m, 1 H), 7.09 – 7.16 (m, 2 H), 7.02 – 7.07 (m, 1 H), 5.95 (s, 1 H), 5.29 (s, 2 H), 4.33 (q, 2 H), 1.36 (t, 3 H).

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENHOWE, Paul Allen; SHEPPECK, James Edward; NAKAI, Takashi; IYER, Karthik; PERL, Nicholas Robert; RENNIE, Glen Robert; WO2015/89182; (2015); 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 3650-78-0 as follows. category: esters-buliding-blocks

To a stirred solution of benzyl bromide (27 mL, 227 mmol) in acetone at r.t. was added tetrahydrothiophene (10.0 mL, 1 14 mmol). The solution was stirred for 16 h and the resulting precipitate filtered and washed with acetone (3 x 50 mL) and dried under air, to give 1 -benzyltetrahydrothiophenium bromide as a white solid (51 .9 g, 88%). [00164] A mixture of 1 -benzyltetrahydrothiophenium bromide (3.39 g, 13.1 mmol) and (?)-methyl 3-(4-bromophenyl)acrylate (2.10 g, 8.71 mmol) in DCM (50 mL) was cooled to -78C and slowly treated with LiHMDS (13.1 mL, 1 M solution in THF) (via syringe pump, 1 mL/h). After complete addition, the mixture was warmed to r.t., stirred for 16 h and was quenched with H20 (50 mL). The biphasic mixture was separated and the organic layer washed with brine (2 x 50 mL), dried (MgS04) and concentrated. Purification by flash silica column chromatography (gradient elution i-hex to 5% EtOAc in i-hex) gave the title compound as a colourless oil (600 mg, 20%). LCMS (ES+) 332, 334 (M+H)+.

According to the analysis of related databases, 3650-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; LUCKHURST, Christopher, A.; BURLI, Roland, W.; STOTT, Andrew, J.; BRECCIA, Perta; WO2014/14900; (2014); A1;,
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Reference of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of methyl 3-bromo-2-methylbenzoate (500 mg, 3.3 mmol), NBS (770.4 mg, 4.3 mmol), and di-benzoyl peroxide (BPO, 80.7 mg, 0.3 mmol) in 1,2-dichloroethane (10 mL) was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over NaSO4, filtered and concentrated to give a crude product (683.2 mg, 89.6%), which was used in the next step reaction without further purification.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Qing; Meng, Liuwei; Zhou, Siru; Deng, Xiaoyan; Wang, Na; Ji, Yi; Peng, Yichun; Xing, Junhao; Yao, Gongmei; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 509 – 523;,
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Related Products of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

(iii) Methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate Under ice-cooling, 1.53 g (7.97 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a DMAc (5 mL) solution comprising 1.45 g (6.64 mmol) of [3-(furan-3-yl)phenoxy]acetic acid, 1.60 g (6.97 mmol) of methyl 2-amino-5-bromobenzoate, and 1.08 g (7.97 mmol) of 1-hydroxybenzotriazole, and the mixture was stirred at room temperature for 4 hours. Under ice-cooling, 1.63 g (19.9 mmol) of 1-methylimidazole was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was stirred for 1 hour. The precipitates were collected by filtration and washed with water and IPE, followed by drying under reduced pressure at 50 C. for 3 hours, thereby giving 2.30 g of methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 81%). 1H-NMR (CDCl3) delta: 3.97 (3H, s), 4.68 (2H, s), 6.72 (1H, dd, J=1.7, 1.0 Hz), 6.97 (1H, ddd, J=7.9, 2.6, 1.0 Hz), 7.19 (1H, ddd, J=7.9, 1.5, 1.0 Hz), 7.23 (1H, dd, J=2.6, 1.5 Hz), 7.35 (1H, t, J=7.9 Hz), 7.49 (1H, t, J=1.7 Hz), 7.67 (1H, dd, J=9.0, 2.4 Hz), 7.76 (1H, dd, J=1.4, 1.0 Hz), 8.19 (1H, d, J=2.4 Hz), 8.74 (1H, d, J=9.0 Hz), 12.08 (1H, s).

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-amino-5-bromobenzoate, its application will become more common.

Reference:
Patent; RENASCIENCE CO., LTD.; US2012/22080; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6091-64-1, name is Ethyl 2-bromobenzoate, 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 6091-64-1, Quality Control of Ethyl 2-bromobenzoate

General procedure: Then, the corresponding ester was refluxed with 85% hydrazine monohydrate in ethanol to get hydrazide 1.

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

Reference:
Article; Li, Chao; Liu, Jia-Chun; Li, Ya-Ru; Gou, Cheng; Zhang, Mei-Ling; Liu, Hong-Yan; Li, Xiao-Zhen; Zheng, Chang-Ji; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 25; 15; (2015); p. 3052 – 3056;,
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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 79669-50-4 as follows. SDS of cas: 79669-50-4

Compound BB-4A-2 (1.00 g, 4.37 mmol), compound BB-1A (1.40 g, 4.37 mmol) and potassium carbonate (1.81 g, 13.10 mmol) were dissolved in 1,4-dioxane (10 mL) and water (3 mL) under nitrogen atmosphere, followed by addition of (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride dichloromethane complex (356.50 mg, 436.55 mumol). The reaction mixture was stirred for 10 hours at 90 C under nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature and concentrated under reduced pressure, followed by addition of water (10 mL) and extraction with ethyl acetate (10 mL¡Á3). The organic phases were combined, washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered to remove the desiccant and concentrated under reduced pressure. The insoluble material was removed by filtration, and the obtained residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate=100/1, 9/1) to obtain the title compound BB-4A-3 (yellow solid, 1.00 g, yield 59.74%). 1H NMR (400MHz,CDCl3) delta: 8.03 (d, J=2.0 Hz, 1H), 7.51 (dd, J=1.9, 7.9 Hz, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.21 – 7.17 (m, 1H), 6.93 (d, J=8.8 Hz, 2H), 4.11 – 4.08 (m, 2H), 3.84 (s, 3H), 3.74 (t, J=4.9 Hz, 2H), 3.48 (t, J=6.7 Hz, 2H), 2.55 (s, 3H), 1.55 – 1.50 (m, 2H), 1.36 – 1.28 (m, 2H), 0.86 (t, J=7.4 Hz, 3H).

According to the analysis of related databases, 79669-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Formula: C8H15BrO2

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1 .15 g, 6.87 mmol) and Cs2C03 (13.43 g, 41.2 mmol) in DMF (45 ml.) is stirred at rt for 30 min before tert.-butyl 4- bromobutanoate (1 .55 g, 6.95 mmol) is added. The orange suspension is stirred at 65C for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1 .55 g, 6.95 mmol) is added and stirring is continued at 65C for 24 h. The mixture is dilued with water (150 ml.) and extracted three times with DCM (3×50 ml.) and EA (3×50 ml_). The org. extracts are combined, dried over MgS04, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano- 6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR = 1 .01 min, [M+H]+ = no mass detectable; 1 H NMR (D6-DMSO): delta 7.94 (d, J = 1 .7 Hz, 1 H), 7.75 (d, J = 1.3 Hz, 1 H), 3.95 (t, J = 6.3 Hz, 2 H), 2.46 (t, J = 7.2 Hz, 2 H), 2.30 (s, 3 H), 1.98 (quint, J = 6.6 Hz, 2 H), 1 .41 (s, 9 H).

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; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; LESCOP, Cyrille; MATHYS, Boris; MORRISON, Keith; MUELLER, Claus; NAYLER, Oliver; STEINER, Beat; WO2012/98505; (2012); A1;,
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Related Products of 23877-12-5, The chemical industry reduces the impact on the environment during synthesis 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, I believe this compound will play a more active role in future production and life.

Reference Example 58 To a solution (50 ml) of (6-chloropyridin-3-yl)(2-hydroxy-4-methoxyphenyl)methanone (4.17 g) in N,N-dimethylformamide were added tert-butyl 2-bromo-2-methylpropanoate (17.6 g), potassium carbonate (10.9 g) and magnesium sulfate (5.70 g), and the mixture was stirred at 95C for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:7, v/v) to give tert-butyl 2-{2-[(6-chloropyridin-3-yl)carbonyl]-5-methoxyphenoxy}-2-methylpropanoate as a colorless oil. Recrystallization from ethyl acetate-hexane gave colorless prism crystals (3.49 g, 54%). melting point 128 – 129C.

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, tert-Butyl 2-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1911738; (2008); 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. 130754-19-7, name is Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

500 mg of ethyl 2-(4-chlorophenyl)-2,2-difluoroacetate, adding 10 mL of methanol, 10 mL of water, 560 mg (10 mmol) of potassium hydroxide, stirring at room temperature for two hours, then evaporating methanol to remove water by rotary evaporation The layer was adjusted to pH 5 with hydrochloric acid to precipitate a white solid. Filtration in vacuo gave 270 mg of 2-(4-chlorophenyl)-2,2-difluoroacetic acid white powder. Used directly in the next step of the reaction.

According to the analysis of related databases, 130754-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhejiang University; Yang Chunhao; Shao Jimin; Zhu Weiliang; Xu Zhijian; Wang Meng; Chen Xinhuan; Hou Chuanwei; Liu Xia; Li Bo; Chen Kaixian; (47 pag.)CN105085433; (2019); B;,
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Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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. Recommanded Product: 135484-83-2

Into a 1000-mE 3-necked round-bottom flask, was placed methyl 2-amino-4-bromobenzoate (5.0 g, 21.73 mmol, 1.00 equiv), a solution of sulfuric acid (20%) (20 mE) in water (100 mE). This was followed by the addition of a solution of NaNO2 (1.8 g, 26.09 mmol, 1.20 equiv) in water (20 mE) dropwise with stirring at 00 C., after stirred 1 hour at 00 C. To this was added a solution of iodopotassium (7.21 g, 43.43 mmol, 2.00 equiv) in water (30 mE) dropwise with stirring at 00 C. The resulting solution was stirred for 1 hour at 00 C. in a water/ice bath. The reaction was then quenched by the addition of 200 mE of water/ice. The resulting solution was extracted with ethyl acetate (100 mEx3) and the organic layers combined. The resulting mixture was washed with brine (100 mExl). The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/5). This resulted in 5.97 g (81%) of methyl 4-bromo-2-iodobenzoate as light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 135484-83-2, its application will become more common.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); A1;,
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