Category: 74586-53-1

Reference of 74586-53-1, A common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

Example 1.54 N-(3-Bromo-5-methylphenyl)-4-(difluoromethyl)-5-fluoropyrimidin-2-amine 2-Chloro-4-(difluoromethyl)-5-fluoropyrimidine (30 g, 162 mmol, 1.00 equiv) p- TsOH (37 g, 215 mmol, 1.33 equiv), 1,4-dioxane (600 mL), 3-bromo-5-methylaniline (46 g, 247 mmol, 1.53 equiv) were added into a 1000-mL pressure tank reactor purged and maintained with an inert atmosphere of nitrogen. The resulting solution was stirred for 72 h at 105C. The reaction mixture was cooled to room temperature. The solid was filtered out and the filtrate was concentrated under reduced pressure. The residue was applied onto a silica gel and purified column chromatography on silica (1 :20 ethyl acetate/petroleum ether) to afford N-(3-bromo-5- methylphenyl)-4-(difluoromethyl)-5-fluoropyrimidin-2-amine as a yellow solid. MS ESI calc’d. for Ci2H10BrF3 3 [M+H] + 332/334, found 332/334. NMR (400 MHz, CDC13): delta 8.45 (1H, s), 7.73 (1H, s), 7.21 (1H, s), 7.18 (1H, s), 7.05 (1H, s), 6.63 (1 H, t, J = 53.37 Hz), 2.34 (3H, s).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 74586-53-1, name is 3-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8BrN

To a solution of 3-bromo-5-nitrotoluene (1500g) in glacial acetic acid (11 I) in a nitrogen purged hydrogenation vessel was added 5% platinum on carbon (approx 50% water wet paste) and the mixture was hydrogenated under 4 bar hydrogen pressure at room temperature. On completion of hydrogen uptake the catalyst was removed by filtration and the filtrate split into two equal portions. Each portion was set to stir separately and a solution of potassium cyanate (500g) in water (1.25 I) was added to each over 15 min. After stirring for an additional 15 min water (10 I) was added and the precipitated solid isolated by filtration and washed with water. The water wet cakes were combined and dissolved in hot EtOAc (3 I) and the aqueous phase separated. The organic phase was cooled with stirring to crystallise the product, which was isolated by filtration and washed with fresh EtOAc (2 I) and air dried overnight. Recrystallisation from ETOH (2. 7 I) afforded the title compound. (565G) LC RT=3.9 mins.

According to the analysis of related databases, 74586-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/39766; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 74586-53-1 as follows. name: 3-Bromo-5-methylaniline

A solution of the 3-bromo-5-methylbenzenamine (500 mg, 2.69 mmol), ammonium acetate (207 mg, 2.69 mmol) and water (0.4 mL) in AcOH (1.35 mL) was added during 30 minutes (push serynge) to a solution of formaldehyde (37%w/w in water, 200 pL, 2.69 mmol) and glyoxal (40% w/w in water, 308 pL, 2.69 mmol) in AcOH (1.35 mL) at 70 00 The reaction was stirred at that temperature for 18 hours. The reaction was slowly pored into saturated aqueous sodium bicarbonate. Some water was added and the precipitated solid was filtered. The filtrate was extracted with DCM and the combined organic layers were dried with sodium sulfate, filtered and evaporated and afforded the title compound (378 mg, 1.59 mmol, 59%) as an orange oil.

According to the analysis of related databases, 74586-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, 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.

General procedure: Conventional method: CDI (1.74 g, 0.01 mol) was added to dimethylacetamide solvent (1.0 mL) and were heated to 120-125C for 0.5 h. Cooled the solution to 60-65C and aniline (1.0 g, 0.01 mol) was added. After 1.5 h, HPLC analysis of the crude product showed that the reaction had proceeded to 100% conversion.The reaction solution was cooled to 20-25C and quenched with water (15 mL). The reaction mixture was extracted with isopropyl acetate (2 10 mL). The combined organic layer was washed with 1% aqueous HCl solution (2 10 mL),dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum to give 1.3 g (90%) of N-phenylacetamide (Table 2, entry 1).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chikkulapalli, Anil; Aavula, Sanjeev Kumar; Mona Np, Rifahath; Karthikeyan, Karthikeyan; Kumar C.H., Vinodh; Sulur G., Manjunatha; Sumathi, Shanmugam; Tetrahedron Letters; vol. 56; 24; (2015); p. 3799 – 3803;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, 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. 74586-53-1, name is 3-Bromo-5-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add m-bromoaniline (688mg, 4mmol), intermediate 3-2 (940mg, 5mmol), cuprous iodide (10%), L-proline (L-Pro, 20%) to a 25ml Shrek tube. , Cesium carbonate (2equiv) and dimethyl sulfoxide (0.5M). The resulting mixture was sparged with nitrogen for 10 minutes and stirred at 120 C for 3 days. After cooling, water and ethyl acetate (EA) were added, and the mixture was filtered. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with brine, and the organic phase was dried over anhydrous Na2SO4. Using PE: EA = 10: 1 as the eluent, the obtained solution was purified by silica gel chromatography to obtain intermediate 3-3 (brown viscous liquid, yield 75%).

The synthetic route of 3-Bromo-5-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Jianuolin Optoelectric Technology Co., Ltd.; Hang Xiaochun; Yin Junli; Wang Ying; (66 pag.)CN110551157; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 74586-53-1, name is 3-Bromo-5-methylaniline, belongs to bromides-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 74586-53-1, Quality Control of 3-Bromo-5-methylaniline

[0251] 3-Bromo-5-methylaniline (372.2 mg, 2.0 mmol) was dissolved in aqueous 1 N hydrochloric acid (160 mL), and acrolein diethylacetal (762 mu^, 5.0 mmol) was added. The reaction mixture was heated to reflux for 24 hours. After cooling to room temperature, the dark brown solution was neutralized with solid potassium carbonate and extracted with dichloromethane (3 x 150 mL). Combined organic layers were washed with brine (1 x 150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified on silica gel using a mixture of dichloromethane and methanol (100:0 to 90: 10 gradient) as eluent. The product was obtained as brown oil as a mixture of isomers Int-2 and Int-2A (1.5: 1) in 35% yield. Major isomer: ‘H- MR (500 MHz, CDC13): delta 8.88 (dd, J = 4.2, 1.3 Hz, 1H), 8.46 (d, J = 8.5 Hz, 1H), 7.85 (s, 1H), 7.68 (s, 1H), 7.42 (dd, J= 8.5, 4.2 Hz, 1H), 2.65 (s, 3H); Minor isomer: 1H-NMR (500 MHz, CDC13): delta 8.90 (dd, J = 4.1, 1.4 Hz, 1H), 8.27 (d, J = 8.5 Hz, 1H), 8.14 (s, 1H), 7.48 (s, 1H), 7.42 (dd, J = 8.5, 4.2 Hz, 1H), 2.54 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 74586-53-1, name is 3-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 74586-53-1

Preparative Example 1.2 – N-(3-b yclopropylpyrimidin-2-amine To a solution of 2-chloro-4-cyclopropyl-pyrimidine (12.5 g, 81 mmol) and 3- bromo-5-methylaniline (18.1 g, 97 mmol) in 1,4-dioxane (100 mL) was added pivalic acid (9.3 mL, 81 mmol). The resulting mixture was heated to reflux and left stirring for 10 hours. The mixture was allowed to cool to room temperature and hexanes were added (80 mL). The slurry was filtered and the filtrate was washed with MeOH to afford a portion of N-(3-bromo-5- methylphenyl)-4-cyclopropylpyrimidin-2-amine. The mother liquors were concentrated, absorbed on silica gel and purified by silica gel column chromatography (EtO Ac/Hex) to afford additional N-(3-bromo-5-methylphenyl)-4-cyclopropylpyrimidin-2-amine as a white solid. MS ESI calcd. for C14H15BrN3 [M+H]+ 304 and 306, found 304 and 306.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 74586-53-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; HAIDLE, Andrew, M.; BURCH, Jason; GUAY, Daniel; GAUTHIER, Jacques Yves; ROBICHAUD, Joel; FOURNIER, Jean Francois; ELLIS, John Michael; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; SMITH, Graham; NORTHRUP, Alan, B.; WO2014/31438; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 74586-53-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74586-53-1 name is 3-Bromo-5-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4- dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous saturated sodium bicarbonate solution, followed by extraction with EtOAc (2×2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS ESI calc’d for Ci2H10BrF3 3 [M + H]+ 332, 334, found 332, 334. NMR (400 MHz, CDCI3): delta 8.68 (d, J= 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.33-7.23 (m, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; HAIDLE, Andrew, M.; KNOWLES, Sandra Lee; KATTAR, Solomon, D.; DESCHENES, Denis; BURCH, Jason; ROBICHAUD, Joel; CHRISTOPHER, Matthew; ALTMAN, Michael, D.; JEWELL, James, P.; NORTHRUP, Alan, B.; BLOUIN, Marc; ELLIS, John, Michael; ZHOU, Hua; FISCHER, Christian; SCHELL, Adam, J.; REUTERSHAN, Michael, H.; TAOKA, Brandon, M.; DONOFRIO, Anthony; WO2013/192098; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

INTERMEDIATE 8: N-[3-methyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl]-4- (trifluoromethyl)pyrimidin-2-amineStep 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4-dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous saturated sodium bicarbonate solution, followed by extraction with EtOAc (2×2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-(3- bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS ESI calc’d for Ci2H,oBrF3N3 [M + H]+ 332, 334, found 332, 334. NMR (400 MHz, CDCI3): delta8.68 (d, J= 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.33-7.23 (m, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

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, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; ELLIS, John Michael; FISCHER, Christian; GRIMM, Jonathan; HAIDLE, Andrew, M.; KATTAR, Solomon, D.; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETROCCHI, Alessia; SCHELL, Adam, J.; ZHOU, Hua; WO2012/154519; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary