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S-21 News Share a compound : 1000342-11-9

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.

Application of 1000342-11-9, A common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, molecular formula is C9H10BrNO2, 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.

Methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl) amino) benzoate (2) A reactor was charged with methyl 3-amino-5-bromo-2-methylbenzoate (455.8 g, 1.87 mol), 1,2- Dichloroethane (4.56 L), and acetic acid (535 ml, 9.34 mol). To the mixture were added dihydro-2H-pyran-4(3H)-one (280 g, 2.80 mol) and sodium triacetoxyborohydride (594 g, 2.80 mol) maintaining the internal temperature below 40 C. The mixture was stirred at 25 C for 2.5 h and then the reaction was quenched with a solution of sodium hydroxide (448 g, 11.20 mol) in water (5.61 L). After stirring for 20 minutes at ambient temperature, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (3.65 L). The organic layers were combined, washed with brine (1.5 L), and concentrated under vacuum. The residue was treated with ethyl acetate (1.8 L) and heated to 65-70 C. The mixture was stirred at 65-70 C for 15 minutes to give a clear solution and then treated with n-heptane (7.3 L) maintaining the temperature between 60-70 C. Once the heptane was completely added to the solution, the mixture was held at 65-70 C for 15 minutes and then allowed to cool to 18- 22 C over 3 h. The resulting suspension was stirred at 18-22 C for 4 h, cooled to 0-5 C over 1 h, and held at 0-5 C for 2 h. The precipitate was filtered, washed twice with n-heptane (1.4 L), and dried under vacuum to give the title compound (540 g, 88%). The XRPD pattern of this compound is shown in Figure 17.

Reference:
Patent; EPIZYME, INC.; EISAI R&D MANAGEMENT CO.LTD.; KUNTZ, Kevin, Wayne; HUANG, Kuan-chun; CHOI, Hyeong, Wook; SANDERS, Kristen; MATHIEU, Steven; CHANDA, Arani; FANG, Frank; WO2013/155317; (2013); A1;,
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8-Sep-2021 News Extended knowledge of 1000342-11-9

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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

The 2-methyl-3-amino-5-bromobenzoic acid methyl ester (1.5g, 6 . 1mmol) dissolved in 15 ml chloroform, by adding potassium acetate (0.63g, 6 . 4mmol) and acetic anhydride (1.26g, 12 . 3mmol), stirring the mixture at room temperature for 12 hours. Then added tert-butyl nitrite (2.53g, 24 . 6mmol) and 18-crown -6 (0.57g, 2 . 15mmol), 65 C lower stirring 3 hours. After finishing the reaction, cooling to room temperature, add saturated sodium bicarbonate aqueous solution and dichloromethane, separating, sodium sulfate drying, extraction, concentration to obtain the product.

Reference:
Patent; Sichuan Univeristy; Yu, Luoting; Wei, Yuquan; (54 pag.)CN105037360; (2016); B;,
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Introduction of a new synthetic route about 1000342-11-9

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

Synthetic Route of 1000342-11-9, 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of methyl 5-bromo-3-(ethylamino)-2-methylbenzoate To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (1.0 g, 4.09 mmol) and acetaldehyde (180 mg, 4.09 mmol) in dichloroethane (10 mL), acetic acid (1.47 g, 24.58 mmol) was added and reaction stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.6 g, 12.29 mmol) was added at 0 C., allowed to attain room temperature and stirring continued for 2 h. On completion, reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous sodium bicarbonate solution and dried over sodium sulphate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the desired compound (600 mg, 55%).

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; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
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A new synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate

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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1000342-11-9

[01042] Step 5: methyl l-acetyl-6-bromo-lH-indazole-4-carboxylate[01043] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61.5 mmol) in chloroform (150 mL), was added potassium acetate (6.32 g, 64.4 mmol) and acetic anhydride (12.6 g, 122.9 mmol) and reaction mixture was stirred at room temperature for 12 h. After this time, tert-butyl nitrite (25.3g, 246.1 mmol) and 18-crown-6 (5.7 g, 21.5 mmol) were added and reaction stirred again at 65 C for 3 h. On completion, the reaction mass was cooled to room temperature, diluted with chloroform (500 mL) and washed with sat. sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford the title compound (18 g, 98.3%).

According to the analysis of related databases, 1000342-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
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Discovery of Methyl 3-amino-5-bromo-2-methylbenzoate

Related Products of 1000342-11-9, 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) Methyl 5 -bro -2-methyl-3 -((tetrahydro-2H-pyran-4-yl)amino)benzoate A I L round-bottomed flask was charged with methyl 3-amino-5-bromo-2- methylbenzoate (15.26 g, 62.5 mmol) and dihydro-2H-pyran-4(3H)-one (9.39 g, 94 mmol) in 1 ,2-dichloroethane (DCE) (250 mL) to give a yellow solution at room temperature under nitrogen. Acetic acid (21.47 mL, 375 mmol) was added to the reaction mixture. After 30 min, sodium triacetoxyborohydride (39.8 g, 188 mmol) was added to the reaction mixture. After 3 h, sodium triacetoxyborohydride (39.8 g, 188 mmol) was added to the reaction mixture. The reaction was stirred overnight, at which time it was diluted with water and neutralized with NaHC03 to pH 7. The reaction mixture was extracted with EtOAc (3x). The combined EtOAc layers were stirred with Na2S04 and activated carbon darco for 30 min, then filtered through a pad of Si02 (2″ x 1″) and concentrated. The solids were stirred with ether and filtered to obtain methyl 5-bromo-2-methyl-3- ((tetrahydro-2H-pyran-4-yl)amino)benzoate (15.4 g, 46.9 mmol, 75 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 6.98 (d, J=2.02 Hz, 1 H), 6.94 (d, J=1.77 Hz, 1 H), 5.03 (d, J=8.08 Hz, 1 H), 3.94 – 3.84 (m, 2 H), 3.80 (s, 3 H), 3.64 – 3.51 (m, 1 H), 3.44 (td, J=11.68, 1.89 Hz, 2 H) 2.15 (s, 3 H), 1.84 (dd, J=12.63, 2.02 Hz, 2 H), 1.43 – 1.69 (m, 2 H). MS(ES) [M+H]+ 328, 330.

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; GLAXOSMITHKLINE LLC; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; DONATELLI, Carla, A.; WO2014/107277; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of C9H10BrNO2

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. Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

[01355] Step 4: Synthesis of cis and trans methyl 5-bromo-3-((4-((tert-butoxycarbonyl)amino) cyclohexyl) amino -2-methylbenzoate[01356] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (5.6 g, 26.7 mmol) in methanol (50 mL), acetic acid ( 1 .2 g, 20.57 mmol) was added and reaction stirred at room temperature for 8 h. Then sodium cyanoborohydride (1.6 g, 26.74 mmol) was added at OoC and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography twice eluting with ethyl acetate: hexane to afford (4g , 44%) of less polar cis isomer and (3g, 33%) of the pure more polar trans isomer.

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; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Ester – Wikipedia,
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Share a compound : Methyl 3-amino-5-bromo-2-methylbenzoate

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

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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Ester – an overview | ScienceDirect Topics

Extended knowledge of Methyl 3-amino-5-bromo-2-methylbenzoate

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.

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.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Share a compound : 1000342-11-9

Electric Literature of 1000342-11-9, A common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, molecular formula is C9H10BrNO2, 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.

Some scientific research about 1000342-11-9

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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-amino-5-bromo-2-methylbenzoate

Example 112:Methyl 5-bromo-3-(6-bromohexanamido)-2-methyl benzoateTo a stirred solution of 6-bromohexanoic acid (3 g, 15.38 mmol) in DCM (25 mL) at 0 C was added drop-wise solution of oxalyl chloride (1.481 mL, 16.92 mmol) in DCM (10 mL). After complete addition, the reaction mixture was stirred at 0 C and then at RT for 30 mm. After completion of the reaction, solvents were removed, the resulting mixture was dried and was added drop-wise to thepreviously cooled solution of methyl 3-amino-5-bromo-2-methyl benzoate (3.75 g,15.38 mmol) in DCM (30 mL). To the resulting mixture was added triethylamine(4.29 mL, 30.8 mmol) and stirred for 2 h. The reaction mixture was quenched withwater, extracted with DCM and the organic layer was washed with brine solution.The organic layer was dried over anhydrous sodium sulphate and evaporated toobtain a brown residue. The residue was purified by column chromatography(silica gel, 2:8 ethyl acetate: petroleum ether) to yield the title compound.Yield: 4.7 g (72 %); 1H NMR (DMSO-d6, 300 MHz): 6 9.56 (5, 1 H), 7.78 (d, J = 1.8 Hz, 1H), 7.68 (d, J = 1.8 Hz, 1H), 3.84 (5, 3H), 3.55 (t, J = 6.6 Hz, 2H), 2.37 (t, J = 7.2 Hz, 2H), 2.27 (5, 3H), 1 .89 (m, 2H), 1.68 (m, 2H), 1 .49 (m, 2H); MS(ESl+): m/z 422.2 [M+H], HPLC Purity: 99.56 %.