Author: Jessica.F

Application of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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) N-(3-bromophenethyl)-2-chloroacetamide (0164) To a suspension of 2-(3-bromophenyl)ethanamine (10 g, 48.5 mmol, CAS 58971-11-2) and NaHC03 (4.28 g, 50.9 mmol) in dichloromethane (60 mL) was added dropwise chloroacetyl chloride (4.66 mL, 58.2 mmol, CAS 79-04-9) at 0 C during 30 min. The reaction mixture was allowed to warm to room temperature overnight, before being quenched by slow addition of water at 0 C. The organic layer was separated, and washed successively with 10% aqueous HC1 solution and brine, dried (Na2S04), filtered and concentrated in vacuo to afford the title compound (9.38 g) as viscous yellow oil which was used in the next step without further purification.

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECERE, Giuseppe; GALLEY, Guido; NORCROSS, Roger; PATINY-ADAM, Angelique; PFLIEGER, Philippe; (68 pag.)WO2016/30306; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2550-36-9, name is (Bromomethyl)cyclohexane, 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 2550-36-9, category: bromides-buliding-blocks

At RT, 96 g of sodium hydroxide, 45% strength in water (1081 mmol, 1 equivalent), were initially charged in 1170 ml of methanol, 119 g of 2-amino-3-hydroxypyridine (1080 mmol, 1 equivalent) were added and the mixture was stirred at RT for another 10 min. The reaction mixture was concentrated under reduced pressure, the residue was taken up in 2900 ml of DMSO and 101 g of cyclohexylmethyl bromide (1135 mmol, 1.05 equivalents) were added. After 16 h at RT, the reaction mixture was slowly added to 6 l of water and the aqueous solution was extracted twice with in each case 2 l of ethyl acetate. The combined organic phases were washed with in each case 1 l of saturated aqueous sodium bicarbonate solution and water, dried, filtered and concentrated. The residue was stirred with 500 ml of n-pentane, filtered and dried under reduced pressure. This gave 130 g (58% of theory) of the title compound. LC-MS (Method 3): Rt=1.41 min MS (ESpos): m/z=207.1 (M+H)+

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; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; BROCKSCHNIEDER, Damian; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; (50 pag.)US2017/304278; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

65896-11-9, name is 2-Bromo-6-fluoroaniline, belongs to bromides-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. Quality Control of 2-Bromo-6-fluoroaniline

N-(2-Bromo-6-fluorophenyl)pivalamide. 2-Bromo-6-fluoroaniline (43.2 mmol, 8.2 g) was dissolved in pyridine (124 mmol, 10 mL). Pivaloyl chloride (57.15 mmol, 7.0 mL) was added to the mixture. Reaction was stirred at room temperature for 3 hours. Reaction mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed 2×1N HCl, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was treated with hexanes and triturated. Resulting solids were filtered off, washed with hexanes then dried in vacuo. Title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): delta=7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). MS m/e (M+H)+=274.1, 276.1.

The synthetic route of 65896-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/49577; (2007); 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. 583-68-6, name is 2-Bromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 mol% of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 mol% of catalyst 5 was applied.

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 583-68-6.

Reference:
Article; Srinivas, Keesara; Saiprathima, Parvathaneni; Balaswamy, Kodicherla; Ra, Mandapati Mohan; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 162 – 167;,
Bromide – Wikipedia,
bromide – Wiktionary

418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, belongs to bromides-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. Application In Synthesis of 4-Bromo-2-fluoro-5-methylaniline

To a stirred solution of 4-(2-(benzyloxy)ethoxy)-l -methyl- lH-pyrazole-5-carbonyl chloride (0.9 g, 3.05 mmol, 1 equiv) and 4-bromo-2-fluoro-5-methylaniline (0.6 g, 3.05 mmol, 1 equiv) in DCM was added Et3N (0.5 g, 4.58 mmol, 1.5 equiv) at 0 C under nitrogen atmosphere. The resulting solution was stirred for 30 min. The reaction was quenched with water at room temperature. The aqueous layer was extracted with CH2CI2 and the organic layer wasconcentrated under reduced pressure to give the title compound (1 g, 70.84%) as a white solid. LC-MS: (ES, m/z): [M+H]+ 462.

The synthetic route of 418762-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; SUTTON, JR., James Clifford; (0 pag.)WO2019/236766; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 73918-56-6, 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. 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Step (i) of Reference Example 4: N-(4-Bromophenethyl)-2-nitrobenzenesulfonamide Triethylamine 0.7 ml (5.0 mmol) was added to a solution of 500 mg (2.5 mmol) of 2-(4-bromophenyl)ethanamine in tetrahydrofuran (5 ml). 2-Nitrobenzenesulfonyl chloride (664.6 mg, 3.0 mmol) was then added thereto, and the mixture was stirred at room temperature for one hr. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 3 : 1) to give 915 mg (yield 95%) of the title compound. 1H-NMR (400 MHz, CDCl3) delta: 2.80 (2H, t, J = 6.8 Hz), 3.40 (2H, dt, J = 5.9, 6.8 Hz), 5.34 (1H, t, J = 5.8 Hz), 6.97 (2H, ddd, J = 1.9, 2.7, 8.3 Hz), 7.31 (2H, ddd, J = 1.9, 2.7, 8.3 Hz), 7.70 (1H, dt, J = 1.7, 7.6 Hz), 7.74 (1H, dt, J = 1.7, 7.6 Hz), 7.81-7.86 (1H, m), 8.01-8.05 (1H, m).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Bromophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Meiji Seika Kaisha Ltd.; EP2151447; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 941-37-7, name is 1-Bromo-3,5-dimethyladamantane, 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 941-37-7, Application In Synthesis of 1-Bromo-3,5-dimethyladamantane

General procedure: To a solution of thiocarbonate 5g (107 mg, 0.200 mmol) in CPME (0.5 mL) were added dropwise a solution of n-Bu3SnH (75.7 mg, 0.260 mmol) and AIBN (6.6 mg, 0.040 mmol) in CPME (1.5 mL) with a syringe pump over 30 min at 90 C. The resultant mixture was stirred at 90 C for 30 min and concentrated. The residue was purified by 10% w/w K2CO3-silica gel flash column chromatography (hexane?hexane/EtOAc=100/1?50/1?20/1) to give the cis-fused cyclized product 6g (53.6 mg, 0.140 mmol, 70%) and 2.8:1 mixture of cis and trans-fused diastereomers (22.0 mg, 0.0572 mmol, 29%). These isomers were separated by the repeated column chromatography for spectral analysis.

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

Reference:
Article; Kobayashi, Shoji; Kuroda, Hiroyuki; Ohtsuka, Yuta; Kashihara, Takashi; Masuyama, Araki; Watanabe, Kiyoshi; Tetrahedron; vol. 69; 10; (2013); p. 2251 – 2259;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 106-37-6, name is 1,4-Dibromobenzene, A new synthetic method of this compound is introduced below., Safety of 1,4-Dibromobenzene

A solution of n-butyllithium n-hexane (6.6 mL, 10.5 mmol) was added dropwise to a solution of 1,4-dibromobenzene (2.36 g, 10 mmol) THF (20 mL).The reaction was carried out at -78 C under an inert atmosphere of argon for 1 h.Then, carbon tetrachloride (1.05 mL, 5 mmol) was added to the reaction solution and the above conditions were maintained for 2 h.After that, it was slowly heated to room temperature of 27 C and stirred for 12 h.Finally, 30 mL of water was added to interrupt the reaction and extraction was carried out using chloroform.The obtained organic layer was purified by column chromatography to give the intermediate product TBrBen (2.15 g, yield 68.5%).Identification of intermediate products by mass spectrometry, the results are:

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; Yangtze Normal University; Yang Yezi; Yao Chuang; Sun Changqing; (13 pag.)CN108752320; (2018); A;,
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. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

To a stirred solution of benzylamine derivative (1 equiv.) in dry DCM, triethylamine (1 .5 equiv.) and di-tert-butyl dicarbonate (1 -1 .2 equiv.) were added under azote atmosphere. The reaction mixture was stirred at room temperature until completion. Water was then added, the phases were separated and the aqueous phase was extracted once with DCM. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude mixture was then purified by flash column chromatography (0-10% MeOH in DCM) to provide the expected compound. The following compounds are examples illustrating this procedure:; tert-butyl bomophenyl)methyllcarbamate was prepared from 3- bromobenzylamine (2 g, 10.75 mmol). Yield: 2.47g (80%) of the title compound as a white powder

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 10269-01-9.

Reference:
Patent; BCI PHARMA; SURLERAUX, Dominique; AMIABLE, Claire; GUILLON, Remi; (239 pag.)WO2017/191297; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 114078-88-5, name is 5-Bromo-1,2,3-triazine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H2BrN3

To a solution of 5-bromo-1,2,3-triazine (25 g, 156 mmol, 1.0 equiv) in CHCl3 (500 mL) was added 1-(cyclopent-1-en-1-yl)pyrrolidine (25.8 g, 188 mmol, 1.1 equiv). The mixture was stirred at 45 oC for 1 h, diluted with DCM (500 mL), washed with brine (300 mL) twice, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 10/90) to give 11 g (36%) of 3-bromo- 5H,6H,7H-cyclopenta[b]pyridine as a brown solid.

The synthetic route of 114078-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; WANG, Wenyue; ASHCRAFT, Luke W.; (362 pag.)WO2019/144041; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary