Tag: M.W=200-300

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. 112970-44-2, name is 2-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

A mixture of compound 58-1 (200 mg, 989.86 umol, 1 eq.), compound 58-1 (243.76 mg, 1.19 mmol, 1.2 eq.) and EDCI (284.64 mg, 1.48 mmol, 1.5 eq.) in pyridine (3 mL) was stirred at 20 C for 12 hours. The mixture was diluted with EtOAc (30 mL), washed with 1 N hydrochloric acid solution (20 mL*3) dried with sodium sulfate, filtered and concentrated. The residue was purified by prepTLC (PE:EA = 3:1) to give compound 58-2 (150 mg,, yield: 38 %) as brown oil. LCMS: 391.1 [M+ 11

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; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
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Synthetic Route of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Preparation 10 To a reaction vial charged with 3-bromo-2-methoxyaniline (from Step 4 of Preparation 9, 1.12 g, 5.54 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (1.499 g, 7.21 mmol) in dioxane (6 mL) was added aqueous potassium phosphate (2.0 M) (5.54 ml, 11.09 mmol). The resulting mixture was deoxygenated by bubbling argon through the mixture for ~5 min. PdCl2(dppf) (0.122 g, 0.166 mmol) was then added and the mixture was heated at 110 C for 2h. The reaction was cooled, diluted with EtOAc (200 mL), washed with water, brine, dried over anhyd sodium sulfate, filtered and concentrated to afford tan oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate mixtures as the eluant. Fractions containing the desired product were collected, combined, and concentrated under vacuum to afford 0.87 g (77%) of the desired product (Preparation 10) as an oil which solidified upon standing. HPLC (method N) = 0.89 min. LCMS MH+ 204.1.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, belongs to ethers-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 168971-68-4, Formula: C7H3BrF4O

Example 106Preparation of Compound 416CF3Step A – synthesis of compound 206BCompound 206A (2.14 g, 8.3 mmol) was combined with PdCl2(dppf) (0.20 g, 0.25 mmol), bis(pinicolato)diboron (2.52 g, 9.9 mmol), and KOAc (2.43 g, 24 mmol) in DMSO (10 mL). The mixture was put under N2 atmosphere, heated to 1000C and allowed to stir at this temperature for 4 hours, then partitioned with water and 1 : 1 EtOAc/hexane. The organic phase was dried (MgSO4) and concentrated in vacuo, and the resulting residue was purified using flash column chromatography on silica (10% EtOAc/hexane) to provide compound 206B as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/130581; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, belongs to ethers-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 18800-30-1, HPLC of Formula: C8H8Br2O

4-(4-methoxybenzoyl)piperidine (1.2 g, 5.3 mmol),1-(2-Bromoethoxy)-4-bromobenzene (1.9 g, 6.9 mmol), KI (1.6 g, 10 mmol) and 30 mL of ethanol were added to a 100 mL eggplant-shaped flask and heated under reflux, and 5 mL of a 20% KOH solution was added dropwise.The addition was completed in 10 minutes. Reflux for 24 hours, evaporate the solvent and dissolve in 30 mL of dichloromethane.The organic layer was washed three times with 20 mL of water, and the organic layer was concentrated.A mixture of ethyl acetate and petroleum ether was used as the eluent.Column chromatography gave 0.60 g of pale yellow solid with a yield of 27.8%

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, 1-Bromo-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southeast University; Zhong Yan; Fang Tiantian; Chen Liyi; (24 pag.)CN110437136; (2019); A;,
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1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-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. Product Details of 1663-61-2

EXAMPLE IV 1-acetyl-5-butyryl-3-(ethoxy-phenyl-methylidene)-2-indolinone 10 g (49 mmol) 5-butyryl-2-indolinone (Ex. 1.2) are stirred in 200 ml acetic anhydride for 5 h at 130¡ã C. Then 35 ml triethyl orthobenzoate are added and the mixture is stirred for a further 4 h at 100¡ã C. Then it is evaporated down and the resulting precipitate is suction filtered, washed and dried. Yield: 11.5 g (62percent of theory) Rf=0.79 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C23H23NO4 (MW=377.438) Mass spectrum: m/z=378 (M+H)+

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209302; (2005); 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 29578-39-0 as follows. COA of Formula: C7H6BrFO

To a suspension of sodium hydride (60% in mineral oil, 600 mg, 15.0 mmol) inDMF (20 mL) at 65 C was slowly added a solution of 4-hydroxy-l -methylpiperidine (1.15 g, 10 mmol) in DMF (7.0 mL). After stirring for 30 minutes, a solution of 3-bromo-5-fluoroanisole (2.05 g, 10 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred at 65 C for 24 h. The reaction mixture was allowed to cool to ambient temperature then was poured into water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were loaded onto a SCX-2 cartridge, which was then washed with acetonitrile then eluted with 2N ammonia in methanol. Concentration of the basic methanolic fractions in vacuo gave the title compound (1.5 g, 50%). 1H NMR (CDCl3, 400MHz): 6.65 (dd, J = 2.2, 1.6Hz, 1H), 6.63 (dd, J = 2.3, 1.6Hz, 1H), 6.37 (dd, J = 2.3, 2.1Hz, 1H), 4.29-4.21 (m, 1H), 3.75 (s, 3H), 2.70-2.61 (m, 2H), 2.31-2.21 (m, 5H), 2.01-1.93 (m, 2H), 1.86-1.75 (m, 2H). LCMS (Method B): RT = 2.1 min, M+H+ = 300.

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); 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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 32338-02-6

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

According to the analysis of related databases, 32338-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Reference of 6793-92-6, These common heterocyclic compound, 6793-92-6, name is 1-Bromo-4-(phenylmethoxy)benzene, 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.

Nanoporous metal gold catalyst (9.8 mg, 0.05 mmol), ethanol (2 mL) and 4-benzyloxybromobenzene(65.75 mg, 0.25 mmol), cesium carbonate (364.3 mg, 1.125 mmol) was added to the reaction kettle, and hydrogen (40 bar) was added.Heat stirring, the reaction temperature is controlled at 100 C, the reaction time is controlled at 90 h, and the reaction solution is extracted with water to obtain 42.32 mg of biphenyl.The yield was 92%.

Statistics shows that 1-Bromo-4-(phenylmethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 6793-92-6.

Reference:
Patent; Dalian University of Technology; Bao Ming; Zhao Yuhui; Feng Xiujuan; Yu Xiaoqiang; Zhang Sheng; (13 pag.)CN109608297; (2019); A;,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6BrFO

a) 3-Bromo-6-fluoro-2-methoxybenzoic acid I45 To a solution of diisopropylamine (5.4 g, 53.7 mmol) in THF (150 ml.) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 23.4 ml_, 58.5 mmol) dropwise and the mixture was stirred at -78 C for 1 h. The resulting mixture was added dropwise to a solution of 1-bromo-4-fluoro-2-methoxybenzene (10.0 g, 48.8 mmol) in THF (50 ml.) at -78 C and stirring was continued for 90 min. C02 was bubbled through the mixture for 20 min with stirring at -78 C, then allowed to warm to RT and stirred for 15 min. The reaction mixture was adjusted to pH=1 with HCI and the mixture was diluted with water and extracted with DCM (500 ml_). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH = 100/1 to 30/1) to give the title compound (8.0 g, 66%) as a colorless oil. LCMS-D: Rt2.12 min; m/z 248.9/250.9 [M+H]+.

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: ((3-Bromopropoxy)methyl)benzene

To a solution of methyl [2- (4-HYDROXYPHENOXY)-2-METHYLBUTANOATE] (5g, 22. [32MMOL)] in 30mL [DMF] was added cesium carbonate (8.7g, 26. [7MMOL)] followed by benzyl 3-bromopropyl ether (7.7g, 33.6mmol). The solution was stirred at 45 [XB0;C] for 24hr, cooled and poured over water. Extraction with AcOEt followed by washing the extracts with water, drying over anhydrous [NA2SO4] and concentrating under reduced pressure gave the crude residue. Purification over silica gel using AcOEt/hexanes furnished the desired alkylated derivative (8.25g). This product was taken up in [MEOH] (75mL) and hydrogenated over 10percent [PD/C] at 40psi to provide methyl [2- (4- (3-HYDROXYPROPOXY)] phenoxy) -2-methylbutanoate (6.23g, quantitative). [‘H-NMR] [(400MHZ,] [CDC13)] : [8] 6.82 (d, 2H, J=9.4Hz), 6.78 (d, 2H, J=9.2Hz), 4.08 (t, 2H, J=6. [1HZ),] 3.87 (t, 2H, J=6Hz), 3.79 (s, 3H), 2.06-1. 92 (m, 4H), 1.44 (s, 3H), 0.99 (t, 3H, J=7.4Hz).

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/10992; (2004); A1;,
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