Tag: M.W=200-300

Electric Literature of 126430-46-4, These common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, 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.

REFERENCE EXAMPLE 26 A mixture of benzyl 4-bromobutanoate (58.6 diethylamine (58.3 g) and dichloromethane (1000 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate gave benzyl 4-(N,N-diethylamino)butanoate (33.8 g, 60%). NMR (delta ppm in CDCl3): 0.99 (6H,t,J=7.2 Hz), 1.78 (2H,quintet,J=7.2 Hz), 2.39 (2H,t,J=7.2 Hz), 2.49 (4H,q,J=7.2 Hz), 5.11 (2H,s), 7.30-7.41 (5H,m).

The synthetic route of 126430-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5650410; (1997); A;,
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These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-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. Formula: C9H10BrNO2

Example 18:Methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoateTo a solution of the compound of example 17 (15 g, 61.5 mmol) in DOE (100 ml) were added dihydro-2H-pyran-4(3H)-one (11.35 mL, 123 mmol) and acetic acid (21 .11 mL, 369 mmol) and stirred at RT for 2h. The reaction mass was cooled to 0 00 and sodium triacetoxyborohydride (39.1 g, 184 mmol), was addedlot wise in 1 h which was left to stir at RT for 16h. After completion of the reaction, water was added and extracted with ethyl acetate. The compound was adsorbed on silica and purified by column chromatography (silica gel, 10-80 % ethyl acetate in petroleum ether) to yield the title compound.Yield: 15.1 g (73.6 %); 1H NMR (DMSO-d6, 300 MHz): 66.97-6.93 (m, 2H),3.87-3.85 (m, 2H), 3.80 (5, 3H), 3.59-3.55 (m, 1H), 3.46-3.41 (m, 2H), 2.14 (5,3H), 1.84-1.82 (m, 2H), 1.56-1.53 (m, 2H);MS (ESl+): m/z 329.1 [M+H] HPLO Purity: 98.3 %.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, Safety of Methyl 2-bromo-4-fluorobenzoate

Under a nitrogen atmosphere, a solution of compound 46 (11 g, 47.30 mmol) in 210 mL of toluene was added to 12 mL of water, K3PO4 (20 g, 94.59 mmol) and ethylboronic acid (7 g, 94.59 mmol), followed by the addition of Pd(OAc)2 (149 mg, 0.66 mmol). The mixture was heated to 100C, reacted for 3 hours, and then cooled to room temperature. After filteration, the filter cake was washed with ethyl acetate, and the organic phase was collected and purified by column to obtain a total of 8.3 g of the title compound 47 with a yield of 96.6%.

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; Shenzhen Targetrx, Inc.; WANG, Yihan; LI, Huanyin; (30 pag.)EP3415518; (2018); A1;,
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Application of 1459-96-7, 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 1459-96-7 as follows.

A solution of dimethyl bicyclo[2.2.2]octane-l,4-dicarboxylate (58.0 g, 0.25 mol) in methanol (600 mL) was heated under reflux. To this solution was added a solution of potassium hydroxide (9.8 g, 0.175 mol) in methanol (100 mL) and water (12 mL) over 30 minutes. The reaction mixture was refluxed for 24 h. The solvent was then removed and the residue was diluted with water. The aqueous solution was extracted with ethyl acetate (2 x200 mL) to recover starting material (22.0 g), and the aqueous layer was acidified to pH 3 by addition of hydrochloric acid. A precipitate was formed and extracted with ethyl acetate (3 x 300 mL). The combined extracted were washed with brine, dried over sodium sulfate and concentrated to give the titled product (30.0 g, 0.14 mol, 55 % yield).1H NMR(400 MHz, CDCI3) delta ppm 3.65 (s, 3H), 1.81 (s. 12H); MS (ESI) m/z 211.3 [M-H]”.

According to the analysis of related databases, 1459-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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Related Products of 1000342-11-9, The chemical industry reduces the impact on the environment during synthesis 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1 : Synthesis of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl) amino)cyclohexyl)-amino)-2-methylbenzoate: [0671] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (860 g, 3.53 mol) and tert-butyl (4-oxocyclohexyl)carbamate (904.6 g, 4.24 mol) in dichloroethane (1 L), acetic acid (1274 g, 21.23 mol) was added and reaction was stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2250 g, 10.61 mol) was added at 0 C and reaction was stirred at room temperature for 16 hours. On completion (monitored by TLC), reaction was quenched with aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with dichloromethane (1.5 L X 3). The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (100-200 mesh size) eluting with 2, 4, 6 & 8% ethyl acetate in hexane to remove maximum cis isomer. This afforded 945 g of mixture of cis and trans isomers (40:60 by HPLC). The trans isomer was purified by repetitive recrystazlisation with ethyl acetate: hexane (1 :2) to afford 480 g of pure trans isomer as white solid with 99% purity.

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 3-amino-5-bromo-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
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Application of 14062-25-0, 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of ester (20 mmol, 1.0 equiv) in toluene (40 mL) was addedparaformaldehyde (1.80 g, 60 mmol, 3.0 equiv), K2CO3 (8.29 g, 60 mmol, 3.0 equiv),n-Bu4NI (370.0 mg, 1.0 mmol, 0.05 equiv). The reaction mixture was heated to 60 Covernight. After the finish of reaction monitored by TLC, the reaction was cooled toroom temperature, water was added and the aqueous layer was extracted with Et2O(40 mL ¡Á 3). The combined organic layer was dried over anhydrous Na2SO4,concentrated in vacuo. The resulting residue was purified by column chromatographyto give the corresponding acrylate intermediate as a colorless oil. Then, a solution ofsubstituted amine (20 mmol, 2.0 equiv)in THF (13.0 mL) at 0C was added a solutionof corresponding acrylate (10 mmol, 1.0 equiv) in THF (7.0 mL) via addition funnel.The reaction mixture was allowed to warm to ambient temperature then stirred atroom temperature for 24h, and concentrated under vacuum. The resulting residue waspurified by column chromatography to give the corresponding intermediate as a oil.Then to a solution of the oil in dichloromethane (20.0 mL) were added di-tert-butyldicarbonate (2.40 g, 11 mmol) and DMAP (122.0 mg, 1 mmol), and the mixture wasstirred at room temperature for 24h. Saturated aq. NH4Cl was added to the mixtureand the resulting mixture was extracted with dichloromethane. The combined organiclayer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo.The resulting residue was purified by column chromatography to give thecorresponding intermediate as a colorless oil. Then to a solution of the resulting oil inTHF/H2O (5 mL/5 mL) was added LiOH (1.20 g, 50 mmol, 5 equiv). The reactionmixture was heated at 60 C overnight. After cooling to room temperature, thereaction was acidified using aqueous HCl (6 M), and the aqueous layer was extractedwith Et2O (20 mL ¡Á 3). The combined organic layer was washed with water and brine,dried over Na2SO4, and concentrated in vacuo to give the resulting product 4a-j as acolorless crystal, using for the next step without further purification.

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

Reference:
Article; Guo, Li; He, Gu; Pan, Zhaoping; Wu, Fengbo; Yu, Meng; Zeng, Minghui; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, A new synthetic method of this compound is introduced below., SDS of cas: 609-12-1

A mixture of 10 g commercially available ethyl-2-bromo isovalerate and 17.8 g sodium iodide in 150 ml acetone are heated to reflux over night. The solvent is removed under reduced pressure. Dichloromethane is added to the residue and the solution is washed with an aqueous solution (10 %) of sodium thiosulfate and brine. The organic layer is dried and the solvent is removed under reduced pressure. 11.34 g (93 %) of the title compound are obtained as a yellowish oil. MS: m/z (M+) = 255.9

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; 4SC AG; WO2009/24613; (2009); A1;,
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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. 25542-62-5, name is Ethyl 6-bromohexanoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Anhydrous LiCl (1.14 g, 26.89 mmol) was dried in a reaction tube at 160 C. for 20 min under high vacuum. Zn powder (1.75 g, 26.89 mmol) was added under argon and the mixture was dried again at 160 C. under high vacuum. The reaction tube was evacuated and filled with argon three times. THF (15 mL) was added and the Zn was activated with 1,2-dibromoethane (0.06 mL, 0.67 mmol) and TMSCl (0.017 mL, 0.13 mmol). Ethyl 6-bromohexanoate (3 g, 13.45 mmol) was added and the reaction mixture was stirred at 55 C. overnight. The solution 1 was carefully separated from excess zinc using a dry syringe. 3-bromobenzaldehyde (1.5 g, 8.1 mmol) was dissolved in THF (5 mL). Pd2(dba)3 (0.074 g, 0.08 mmol) and t-Bu3P (0.162 mL, 0.162 mmol, 1M) was added. The solution of the organozincate compound 1 in THF (1.5 equivalent) was added to the reaction. The mixture was stirred for 30 min at it (room temperature) and then quenched with NH4Cl (aq. sat.: aqueous saturated solution). The mixture was extracted with Et2O. The combined organic phase was dried, concentrated and purified by flash chromatography to give the ester 2 (1.95 g, 7.858 mmol, 97%). 1H NMR (250 MHz, CDCl3): delta=9.96 (s, 1H), 7.60-7.72 (m, 2H), 7.37-7.46 (m, 2H), 4.08 (q, J=7.1 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 2.26 (t, J=7.4 Hz, 2H), 1.56-1.71 (m, 4H), 1.26-1.42 (m, 2H), 1.21 (t, J=7.1 Hz, 3H); HRMS (EI+): [M]+ calculated for C15H20O3, 248.1412. found 248.1413.

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; UNIVERSITY DE SANTIAGO DE COMPOSTELA; UNIVERSIDADE DA CORUNA; SERVIZO GALEGO DE SAUDE (SERGAS); PEREZ FERNANDEZ, Roman; SEOANE RUZO, Samuel; MOURINO MOSQUERA, Antonio; MAESTRO SAAVEDRA, Miguel; CASTELAO FERNANDEZ, Jose Esteban; GOGOI, Pranjal; (41 pag.)US2016/297731; (2016); A1;,
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Synthetic Route of 99548-56-8, A common heterocyclic compound, 99548-56-8, name is Methyl 2-bromo-6-methylbenzoate, molecular formula is C9H9BrO2, 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.

7-Bromoisoindolin-l-one was prepared by bromination of methyl 2-bromo-6-methyl benzoate (using N-bromosuccinimide and benzoyl peroxide in refluxing CC14) and treatment of the resulting benzyl bromide with ammonia gas in refluxing ethanol. Further elaboration via the procedure of Example 135 gave the title compound. delta (500 MHz, d6 DMSO): 8.62 (1 H, s), 8.24 (1 H, d, J = 7.3 Hz), 7.96 (2 H, d, J = 8.4 Hz), 7.91-7.85 (2 H, m), 7.71-7.64 (4 H, m), 7.40 (1 H, d, J = 16.5 Hz), 7.25 (2 H, d, J = 16.2 Hz), 7.21 (1 H, d, J = 8.8 Hz), 4.36 (2 H, s).

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; MERCK SHARP & DOHME LIMITED; WO2006/21805; (2006); A1;,
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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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 8-Bromooctanoate

1h: Preparation of Compound 8 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 5 g (1 equivalent) of 4-hydroxybenzonitrile, absolute ethanol 150 mL, and 15.7 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 8-bromooctanoate (10.5 g, 1 equivalent) was then added dropwise over 10 minutes. The resulting mixture was heated to reflux (75 C.) for 72 hours. The reaction mixture was cooled and the solids filtered off. The solvent was removed on a rotary evaporator. The crude residue was dissolved in methylene chloride (200 mL) and washed with saturated NaHCO3 (2*75 mL), H2O (1*100 mL) and brine (1*100 mL). The crude material was then dissolved in ethanol (125 mL) and water (10 mL). LiOH (5 g) was added and the resulting mixture was heated to reflux (75 C.) for 1 hour then stirred at ambient temperature overnight. The solvent was evaporated and 75 mL of H2O was added. The aqueous solution was acidified to a pH of about 3 with concentrated HCl and the flask cooled to 4 C. An off-white colored solid precipitated. This material was collected by vacuum filtration and dried on the high vacuum overnight to give the crude acid. These solids were further purified by recrystallization from Ethyl acetate/hexanes (95/5) and again with chloroform to give 4.5 g of the product, 8-(4-cyanophenoxy)octanoic acid (41% yield). Melting point: 137-140 C. Molecular Formula: C15H19NO3. Combustion analysis: %C: 68.94 (calc’d), 68.57 (found); %H: 7.33(calc’d), 7.13(found); %N: 5.36 (calc’d), 5.28 (found).

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
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