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. 150726-89-9, name is Dimethyl 2-(2-methoxyphenoxy)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 150726-89-9

d) Na (2.3 g) was dissolved in methanol (40 ml) and 2-(3-methoxy-phenyl)-acetamidine hydrochloride (10 g) and (2-methoxyphenoxy)-malonic acid dimethyl ester (12.67 g) were added in succession at room temperature. The mixture was stirred for 5 hours at room temperature, concentrated in a rotary evaporator and the crude product was added to water. The aqueous phase was washed with ethyl acetate, adjusted to pH 1 and the precipitated crystals were sucked off and dried under a high vacuum. There was thus obtained 2-(3-methoxy-benzyl)-5-(2-methoxy-phenoxy)-pyrimidine-4,6-diol as beige crystals. MS: 354 (M)

The synthetic route of 150726-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US5837708; (1998); A;,
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Electric Literature of 23062-51-3, 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. 23062-51-3, name is Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of XVIII-2 (6 g, 24.2 mmol) in anhydrous benzene (60.15 g) was added dropwise to an ice-water cooled suspension of AlCl3 (5.95 g, 45.1 mmol) in benzene (60.15 g) under nitrogen. The resulting reaction mixture was allowed to stirred in the ice bath for 30 min and then at rt overnight. The mixture was heated to 60 C. for 4 h and then allowed to cool to rt and poured into ice and concentrated HCl. The mixture was extracted with EtOAc, washed with brine, separated, and dried over Na2SO4 to leave an orange-brown solid, which was purified by column chromatography (PE:EA=10:1) to afford XVIII-3 (2.3 g, yield: 38.6%).

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 4-bromobicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/200215; (2014); 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 99548-55-7 as follows. Safety of Methyl 4-bromo-2-methylbenzoate

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.

According to the analysis of related databases, 99548-55-7, the application of this compound in the production field has become more and more popular.

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 14273-90-6,Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, 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 11 (0.5g, 1.75mmol) in acetonitrile (30mL) were added Cs2CO3 (2.5g, 5mmol) and methyl 7-bromoheptanoate (0.44g, 2mmol) or methyl 6-bromohexanoate (0.42g, 2mmol). The reaction was warm to 70°C for 2h. The mixture solution was added water (50mL) and extracted with ethyl acetate (30mL×3). The organic layers were combined, washed with brine, dried with Na2SO4 and evaporated. Finally, the resulting residue was purified by column chromatography on silica gel as indicated to give 12a or 12b as white solid.

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

Reference:
Article; Cheng, Gaoliang; Wang, Zhi; Yang, Jinyu; Bao, Yu; Xu, Qihao; Zhao, Linxiang; Liu, Dan; Bioorganic Chemistry; vol. 84; (2019); p. 410 – 417;,
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Synthetic Route of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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 3-bromo-2-methylbenzoate (10.0 g, 43.64 mmol, CAS : 99548-54-6) in benzene (60 ml) were added N-bromosuccinimide (6.1 g, 52.37 mmol) and benzoyl peroxide (1.05 g, 4.36 mmol) at rt. The reaction mixture was stirred at 80 C. for 12 h. The resulting reaction mixture was poured into EtOAc (260 mL) and the organic layer was washed with water (200 ml), separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue. The crude was purified by flash chromatography (eluting at 0-2% ethyl acetate in hexane) to afford 3-bromo-2-(bromomethyl) benzoate (12.0 g, 39.33 mmol). 1H NMR (400 MHz, DMSO-d6) delta 7.92 (dd, J=8.0, 1.3 Hz, 1H), 7.85 (dd, J=7.8, 1.3 Hz, 1H), 7.41 (t, J=7.9 Hz, 1H), 5.02 (s, 2H), 3.87 (s, 3H).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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Application of 706791-83-5,Some common heterocyclic compound, 706791-83-5, name is Methyl 3-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.

To a solution of 3,5-dimethylisoxazol-4-yl)boronic acid (123 mg, 0.869 mmol) and methyl 3-amino-5-bromobenzoate (200 mg, 0.869 mmol) in dimethoxyethane was added sodium carbonate powder (193 mg, 1.83 mmol) in water (1 ml) and palladium tetrakis(triphenylphosphine) catalyst (30 mg, 3 mol%). The reaction mixture was degassed by sparging with a stream of nitrogen and then refluxed for 16 h. The cooled reaction mixture was partitioned between water and ethyl acetate, the organic layer was dried over sodium sulfate, filtered, concentrated and then purified by flash chromatography (1:1 ethyl acetate/hexanes) to give methyl 3-amino-5-(3,5-dimethylisoxazol-4-yl)benzoate as a pale-yellow solid (190 mg, 89%). MS-ESI: m/z calculated for (C13H14N2O3 + H)+ 247.1, found 246.8. 1H NMR (600 MHz, d6-DMSO) delta 7.20 (s, 1H), 7.01 (s, 1H), 6.78 (s, 1H), 5.54 (s, 2H), 3.82 (s, 3H), 2.38 (s, 3H), 2.20 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5-bromobenzoate, its application will become more common.

Reference:
Article; Poncet-Montange, Guillaume; Zhan, Yanai; Bardenhagen, Jennifer P.; Petrocchi, Alessia; Leo, Elisabetta; Shi, Xi; Lee, Gilbert R.; Leonard, Paul G.; Geck Do, Mary K.; Cardozo, Mario G.; Andersen, Jannik N.; Palmer, Wylie S.; Jones, Philip; Ladbury, John E.; Biochemical Journal; vol. 466; (2015); p. 337 – 346;,
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Application of 41727-48-4,Some common heterocyclic compound, 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, molecular formula is C8H7Cl2NO2, 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.

3.12 g (0.078 mol) of sodium hydroxide was added to a solution of 10.33 g (0.039 mol) of methyl 4-amino-3,5-dichlorobenzoate in 40 mL of DMF, followed by addition of 10.37 g (0.039 mol) of 2,4,5,6-tetrachloroisophthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90 C.)=1:4, as an eluent) to give 13.65 g of compound B-62 as yellowish solid, m.p. 229-231 C. [0147] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) delta (ppm): 3.96 (s, 3H, CH3), 6.92 (s, 1H, NH), 8.11 (s, 2H, Ph-2,6-2H).

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-amino-3,5-dichlorobenzoate, its application will become more common.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H13BrO4

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.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Reference of 179022-43-6, 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 179022-43-6 as follows.

Example 27: 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen-2-yl) azabicyclo[3.2.1]octane-3-carboxylic acid To a solution of methanesulfonic acid 5-(4-methyl-cyclohexyloxy)-naphthalen-2- ylmethyl ester (177 mg, 0.508 mmol) in DMF (2 mL), 8-aza-bicyclo[3.2.1]octane-3- carboxylic acid methyl ester HCl salt (208.38 mg, 1.0131 mmol) was added, followed by cesium carbonate (495.14 mg, 1.5197 mmol). The reaction was then heated at 80 C for lh. After cooled down, the reaction mixture was diluted with EtOAc, washed with water (2x). The organic phase was then separated, dried and concentrated. The crude was purified by HPLC, removed the solvent, the ester was then dissolved in tetrahydrofuran (2.3 mL, 29 mmol) , treated with 1.0 M of lithium hydroxide in Water(3.5 mL, 3.5 mmol) at rt overnight. Acidified with 1NHC1, the organic layer was dried and concentrated. The crude was then purified by HLPC to give 8-((5-((cis-4-methylcyclohexyl)oxy)naphthalen- 2-yl)methyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid as a white powder (132.9 mg, 64% ). LCMS: RT 1.40 min.; MH+ 408.1. 1H NMR (400 MHz, METHANOL-d4) delta 8.38 (d, J = 8.72 Hz, 1H), 7.98 (s, 1H), 7.60 (d, J = 10.48 Hz, 1H), 7.46 (d, J = 4.96 Hz, 2H), 6.92 – 7.08 (m, 1H), 4.85 (br. s., 1H), 3.80 – 4.45 (m, 2H), 3.37 (s, 2H), 1.35 -2.81 (m, 18H), 1.00 (d, J = 5.65 Hz, 3H).

According to the analysis of related databases, 179022-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; SUN, Lihong; XIN, Zhili; ZHANG, Lei; WO2014/25708; (2014); A1;,
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Related Products of 55666-42-7, 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. 55666-42-7, name is tert-Butyl 2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

tert-Butyl 2-bromobenzoate (129 mg, 0.502 mmol) and anhydrous THF (5 mL) were put into a dried flask inside of which was substituted with argon. The mixture was cooled to -78 C., and then added with 1M sec-BuLi (0.30 mmol), and the mixture was stirred for 20 minutes. The mixture was slowly added with 4,5-dichloro-3,6-diOTBDMS-Si-xanthone (11.3 mg, 0.0200 mmol) dissolved in anhydrous THF (5 mL) at the same temperature, and the mixture was returned to room temperature. The mixture was stirred at room temperature for 1 hour, and then added with 2 N HCl (10 mL), and the mixture was stirred for 20 minutes. The mixture was extracted with dichloromethane, and the organic layer was washed with brine, and dried over Na2SO4. The solvent was removed, then the residue was added with TFA (5 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was removed, and then the residue was purified by HPLC to obtain 2-COOH DCTM (5.7 mg, 0.013 mmol, yield 64%). 1H-NMR (400 MHz, CD3OD): delta 0.83 (s, 3H), 0.98 (s, 3H), 6.85 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 6.98 (d, 1H J=7.8 Hz), 7.51 (td, 1H, J=1.0, 7.6 Hz), 7.60 (td, 1H, J=1.0, 7.6 Hz), 7.90 (d, 1H, J=7.8 Hz) 13C-NMR (100 MHz, CD2COCD2): delta-0.2, 0.5, 90.0, 119.8, 123.6, 124.3, 126.4, 127.1, 127.8, 129.9, 135.1, 136.2, 136.7, 153.6, 158.3, 171.2 HRMS (ESI+): m/z Found 443.0241, calculated 443.0273 for [M+H]+ (-3.2 mmu)

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

Reference:
Patent; THE UNIVERSITY OF TOKYO; Nagano, Tetsuo; Hanaoka, Kenjiro; Koide, Yuichiro; Egawa, Takahiro; Hirabayashi, Kazuhisa; US2013/289256; (2013); A1;,
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