Month: June 2021

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 5445-17-0 as follows. Computed Properties of C4H7BrO2

Example 13 Preparation of (Z)-3-(2-cyclopropylphenyl)-5-methyl-2-((E)-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazono)thiazolidin-4-one (Compound 127C) (Synthesis Method F) To (E)-N-(2-cyclopropylphenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (100 mg, 0.191 mmol) and sodium acetate (63.0 mg, 0.765 mmol) in EtOH (4 mL) was added methyl 2-bromopropanoate (0.026 mL, 0.230 mmol). The reaction was heated to 60 C. overnight. The reaction was then heated to 85 C. for 72 hours. The reaction mixture was diluted with DCM and washed with water. The aqueous layer was extracted with DCM. The organic layers were poured through a phase separator and concentrated. Purification by flash column chromatography provided the title compound as a white solid (32.5 mg, 0.056 mmol, 30%): mp 112-115 C.; 1H NMR (400 MHz, CDCl3) delta 8.58 (s, 1H), 8.32 (s, 1H), 8.22 (d, J=8.3 Hz, 2H), 7.87-7.75 (m, 4H), 7.43-7.32 (m, 4H), 7.26-7.24 (m, 2H), 4.23 (q, J=7.3 Hz, 1H), 1.85-1.78 (m, 4H), 0.90-0.78 (m, 2H), 0.78-0.69 (m, 1H), 0.65-0.55 (m, 1H); ESIMS m/z 578 (M+H).

According to the analysis of related databases, 5445-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Crouse, Gary D.; Sparks, Thomas C.; Dent, III, William H.; McLeod, CaSandra L.; Creemer, Lawrence C.; Demeter, David A.; Fritz, Amanda E.; Fischer, Lindsey G.; Baum, Erich W.; US2012/202687; (2012); A1;,
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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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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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Related Products of 14630-09-2, 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. 14630-09-2, name is Methyl thieno[3,4-b]thiophene-2-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4,6-Dibromo 2-perflurohexyl-thieno[3,4-b]thiophene (14): To a solution of 2.75 g (6.0 mmol) (5) in 15 mL DMF was added dropwise a solution of NBS (2.70 g, 15.0 mmol) in 15 mL DMF under nitrogen protection at dark. The reaction mixture was heated up to 40 C. and kept stirring for 24 h. Then it was cooled down, poured to saturated sodium sulfite solution at ice-water bath, and extracted with dichloromethane. The organic phase was collected and dried by sodium sulfate. Removal of the solvent, and column purification on silica gel using hexane as fluent yielded the target product (14) 3.32 g (90%). 1HNMR (CDCl3): delta 7.20 (1H, s) MS (EI): Calcd, 616.1. found (M+1)+, 616.7.

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 thieno[3,4-b]thiophene-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Chicago; Yu, Luping; Liang, Yongye; US9029499; (2015); B2;,
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Electric Literature of 1117-71-1,Some common heterocyclic compound, 1117-71-1, name is Methyl 4-bromobut-2-enoate, molecular formula is C5H7BrO2, 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 suspension of sodium acetate (3.5 g, 42 mmol) in MeCN (30 ml.) was treated with methyl 4-bromocrotonate (Aldrich) (3.33 ml_, 5 g, 28 mmol) and the mixture was heated to 50 C for 3 d. The mixture was diluted with ether and then filtered. The solid was washed with ether and the combined filtrate and washings was evaporated under reduced pressure. After evaporation the residue was partitioned between ether and water. The organic phase was washed with aqueous sodium bicarbonate, dried over MgSCM, and evaporated under reduced pressure to give a pale orange oil. NMR indicated a mixture of product and starting material, therefore, sodium acetate (3.44 g, 42 mmol) was added to the residual oil, followed by MeCN (10 ml.) and the mixture was heated to 70 C over the weekend. The mixture was concentrated under reduced pressure and the residue was partitioned between ether and water. The organic solution was washed with water, brine, dried (MgSCM) and filtered. The filtrate was evaporated under reduced pressure to give the title compound (3.55 g, 80%) as an orange oil: NMR delta (CDC ) 6.92 (dt, J 16, 5 Etazeta,IotaEta), 6.01 (dt, J 16, 2 Hz, 1H), 4.72 (dd, J 5, 2 Hz, 2H), 3.73 (s, 3H), 2.10 (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 4-bromobut-2-enoate, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BARRETT, Tim; HATLEY, Richard Jonathan Daniel; MACDONALD, Simon John Fawcett; SAKLATVALA, Paula; TSE, Sing Yuen Eric; (35 pag.)WO2017/158072; (2017); A1;,
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14064-10-9, name is Diethyl 2-chloromalonate, 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. Recommanded Product: Diethyl 2-chloromalonate

General procedure: To a suspension of CsF (183 mg, 1.20 mmol) in DMF (2.0 mL) was added Et2Zn (1.0 M in toluene,200 muL, 0.20 mmol) under argon atmosphere at ?40 °C. After being stirred at the same temperature for5 min, diethyl alpha-chloromalonate 4a (32 muL, 0.20 mmol) and 3-methoxy-2-(trimethylsilyl)phenyltriflate (1, 63 muL, 0.24 mmol) were added to the reaction mixture. After being stirred at ?40 °C toroom temperature for 12 h, silica gel (0.5 g) was added to the reaction mixture, and then it wasconcentrated under reduced pressure. Purification of the residue by flash silica gel columnchromatography (EtOAc/hexane = 1:20?1:4) afforded dihydrobenzofuran 7a (58.0 mg, 86percent). Undersimilar reaction conditions, dihydrobenzofurans 7b and 11 were synthesized. Products 8a, 12 and 13were also formed.#10;#10;

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshioka, Eito; Kohtani, Shigeru; Miyabe, Hideto; Molecules; vol. 19; 1; (2014); p. 863 – 880;,
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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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Reference of 105-53-3, A common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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.

Step 1: Into a 5 L 4 necked round bottomed flask was placed a solution of diethyl malonate (300 g, 1.87 mol) and 1,2-dibromoethane (634.5 g, 3.38 mol) in DMSO (1.5 L). The mixture was treated with K2CO3 (1020 g, 7.39 mol) and Bu4NHSO4 (6.4 g, 19 mmol). The resulting solution was allowed to stir for 48 h at room temperature. The reaction mixture was treated with 2 L of H2O and extracted with 1.5 L of EtOAc (3x). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The residue was distilled under 5-10 mmHg vacuum at 64-65 oC. This resulted in diethyl cyclopropane-1,1-dicarboxylate as an oil.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (94 pag.)WO2016/144847; (2016); A1;,
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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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