Month: August 2021

Application of 630-17-1, A common heterocyclic compound, 630-17-1, name is 1-Bromo-2,2-dimethylpropane, molecular formula is C5H11Br, 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: (3 mL) was added the electron-deficient alkene (6 mmol) at room temperature. Under vigorous stirring, NiCl2*6H2O (475 mg,2 mmol) was added to the above mixture. The temperature thenrose to 50 C, and stirring was continued for 20 min. The resulting red-brown Ni(0) complex was cooled to room temperature, and a solution of the alkyl bromide (2 mmol) in pyridine (1 mL) was added dropwise. The mixture was stirred for 0.5 h, and then filtered with a short plug (elution with 50 mL of Et2O) and washed with HCl(1N), water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silicagel to afford desired ester products.

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:
Article; Ouyang, Yan; Peng, Yu; Li, Wei-Dong Z.; Tetrahedron; vol. 75; 33; (2019); p. 4486 – 4496;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, 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 153505-37-4, Application In Synthesis of 4-Bromo-5-fluorobenzene-1,2-diamine

Preparation 38 5-Bromo-6-fluorobenzo[c][1,2,5]thiadiazole 4-Bromo-5-fluorobenzene-1,2-diamine (500 mg, 2.4 mmol) was dissolved in 20 mL chloroform, treated in portions with thionyl chloride (580 mg, 4.9 mmol) and heated to reflux for 20 h. After cooling the mixture was diluted with 60 mL ethyl acetate, washed with 15 mL water, 15 mL saturated NaCl, dried (Na2SO4) and concentrated under vacuum. The material was chromatographed on silica with a 0-30% ethyl acetate-hexane gradient to give the title compound as a white solid (425 mg, 76%): mp 79-82 C.; 1H NMR (400 MHz, CDCl3) delta 8.33 (d, J=6.7 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H); 19F NMR (376 MHz, CDCl3) delta -102.91; EIMS m/z 232.

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; Dow AgroSciences, LLC; Eckelbarger, Joseph D.; Siddall, Thomas L.; Satchivi, Norbert M.; Schmitzer, Paul R.; US2014/274702; (2014); A1;,
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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, A new synthetic method of this compound is introduced below., Product Details of 2862-39-7

60% NaH (0.215 g, 5.39 mmol) was suspended in DMF (4 ml) and the suspension was stirred at room temperature under nitrogen. A solution of N-(3-allyl-4-hydroxyphenyl)acetamide (1 .03 g, 5.39 mmol) in DMF (5 ml) was added and the brown mixture was stirred for 15 min. 2-bromo- Nu,Nu-dimethylethanamine, hydrobromide (0.627 g, 2.69mmol) was added as a solid and the mixture was stirred at room temperature for 48h. Additional 60% NaH (0.215 g, 5.39 mmol) was added followed by addition of 2-bromo-N,N-dimethylethanamine, hydrobromide (0.627 g, 2.69mmol) and the reaction was stirred for 18h at room temperature. Added an additional 1 .0 eq of NaH (215 mg) and stirred 1 hour at room temperature. The reaction was poured into ice- water and stirred until the ice had melted. The solution was transferred to a separatory funnel and the pH was adjusted to 8 using 2M HCI. The solution was extracted with ether and the ether was washed with 2M NaOH, water, dried over sodium epsilonmubetabeta, filtered, and concentrated. The GammaThetaepsilonmuIota-Gamma^ solid was purified via silica gel chromatography (Biotage Isolera, 24 g column, 0-15% MeOH:DCM over 45 min, loaded as a solution in DCM) to give the desired product (88.0 mg, 6%) as a pale yellow solid. LC-MS (ES) m/z = 263.2 [M+H]+ NMR (400 MHz, DMSO-d6) delta ppm 1 .99 (s, 3 H) 2.22 (s, 6 H) 2.62 (t, J=5.75 Hz, 2 H) 3.28 (d, J=6.85 Hz, 2 H) 4.01 (t, J=5.87 Hz, 2 H) 4.97 – 5.10 (m, 2 H) 5.92 (ddt, J=16.93, 10.09, 6.79, 6.79 Hz, 1 H) 6.89 (d, J=8.80 Hz, 1 H) 7.28 (d, J=2.45 Hz, 1 H) 7.40 (dd, J=8.80, 2.69 Hz, 1 H) 9.71 (s, 1 H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DUFFY, Kevin J.; PARRISH, Cynthia Ann; ATOR, Laura E.; BASKARAN, Subramanian; DARCY, Michael Gerard; OPLINGER, Jeffrey Alan; RALPH, Jeffrey M.; RIDGERS, Lance Howard; TIAN, Xinrong; ZHANG, Cunyu; (225 pag.)WO2019/53617; (2019); A1;,
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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3BrF2

Under N2 protection, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 ml), cooledto -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(66 ml, 1.3 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (10 g, 39 mmol) was dissolvedin dry tetrahydrofuran (100 ml), and added dropwise to the reaction solution while the temperature was maintained at-10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4 hours. Thetemperature was lowered to about -10C, and a saturated ammonium chloride solution (40 ml) was added dropwise,followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allow settlingand partitioning. The aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (30 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) = 50:1 to8:1), to obtain a light yellow solid 1E (10.1 g, yield 83.5%).MS m/z (ESI): 210.1 [M-99].

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; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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.

Under nitrogen protection, the product of step 1 and 2.5 equivalents of m-bromophenylacetylene and 0.05 equivalent of cuprous iodide in a solution of diisopropylamine and dichloromethane (volume ratio 1:10) was reacted under nitrogen atmosphere at room temperature for 24 h . The product was isolated on a silica gel column and the yield was 75-80%.

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Ni, Jun; Gai, Xuqiao; Kang, Jiajia; Xu, Liang; (7 pag.)CN105732721; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, 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 30273-40-6, COA of Formula: C8H10BrN

Into a 100 mL 3-necked round-bottom flask was added 4-bromo-2,5-dimethylaniline (3.3 g, 16.50 mmol, 1 equiv), DCM (50 mL), and Et3N (3.3 g, 32.61 mmol, 1.98 equiv). To the above mixture l-(2-(benzyloxy)ethyl)-4-methyl-lH-pyrazole-5-carbonyl chloride (4.6 g, 16.50 mmol, 1 equiv) in 20 mL of DCM was added dropwise at 0 C. The resulting mixture was stirred for additional 1 h at room temperature. The reaction mixture was quenched with water and the aqueous layer was extracted with CH2CI2. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was re-crystallized from MeOH (50 mL) to afford (5.4 g, 73.97%) of the title compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 442.

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; 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

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 solution of 3-bromo-4-fluoroaniline (1.9 g, 10.00 mmol) and 5- (methoxymethylene)-2,2-dimethyl- 1,3 -dioxane-4,6-dione (2.234 g, 12.00 mmol) in dioxane (5 mL) was heated to 120 C for 20 minutes. The reaction mixture is then cooled to room temperature and diluted with 50 ml of dietheyl ether. The solid was filtered and dried to give 5 -(((3 -bromo-4-fluorophenyl)amino)methylene)-2,2-dimethyl- 1,3 -dioxane4,6-dione (2.77 g, 8.0 mmol, 80%). ?HNMR(400 MHz, DMSO-d6) oe 11.23 (br d, J=14.4 Hz, 1H), 8.53 (d, J=14.5 Hz, 1H), 8.06 (dd, J=6.0, 2.8 Hz, 1H), 7.69 – 7.61 (m, 1H), 7.44 (t, J=8.7 Hz, 1H), 1.73 – 1.63 (m, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-(tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1 .37 mmol) in anhydrous DMF (5 mL) was added K2003 (379 mg, 2.74mmol) and (bromomethyl)cyclohexane (364 mg, 2.06 mmol). The reaction mixture was stirred at 60C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC-MS to yield 7-(cyclohexylmethyl)-3-(tetrahydro-2H-pyran-4-yl )imidazo[1 ,5-a]pyrazin-8(7H)-one 240 mg (55%).1H NMR (DMSO-d6, 400 Mhz): 7.62 (s, 1H), 7.47 (d, J= 6.0 Hz, 1H), 6.84 (d, J= 6.2 Hz,1H), 3.91-3.88 (m, 2H), 3.60 (d, J= 7.2 Hz, 2H), 3.48-3.42 (m, 2H), 3.30-3.29 (m, 1H), 1.78-1.52 (m, 1OH), 1.10-1.06 (m, 3H), 0.93-0.91 (m, 2H).LC-MS: (mlz) 316.2 (MH) tR (minutes, method 3) = 2.44 minutes.

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 54962-75-3, 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 17 10-(3-amino-5-triflouro-phenyl)-5,8-Dioxa-10-azadispiro[2.0.4.3]undecane 3-Bromo-5-trifouroaniline (200 mg) was mixed with DIPEA (1.5 eq) in DCM (10 ml) at 0 C. To the reaction was added benzylchloroformate (1.1 eq) and stirred at RT for one hour. The reaction was washed with water, brine and dried over Na2SO4 then evaporated. The residue was purified by column chromatography to give the product (190 mg) that was mixed with 5,8-Dioxa-10-azadispiro[2.0.4.3]undecane (75 mg), Pd(dbda)3 16 mg), X-Phos (28 mg) and t-BuONa (50 mg) in toluene (15 ml). The reaction was heated at 60 C. overnight and evaporated and purified on silica gel column to give the 10-(3-CBZ-amino-5-triflouro-phenyl)-5,8-Dioxa-10-azadispiro[2.0.4.3]undecane (80 mg). This product was mixed with Pd-C (40 mg, 10%), HCOONH4 (160 mg) and MeOH (10 ml). The reaction was refluxed for one hour and filtered through Celite and evaporated. The residue was mixed with water and extracted with EtOAc then purified with silica gel column to give the titled product. Mass: (M+1), 315

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

Reference:
Patent; Chen, Guoqing Paul; US2007/167470; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

Example 4 7-(Cyclopentylmethyl)-3-propyl-[1,2,4]triazolo[4,3-a]pyrazin-8(7H)-one: To a solution of 3-propyl-[1 ,2,4]thazolo[4,3-a]pyrazin-8(7H)-one (200 mg, 1 .1 mmol) and (bromomethyl)cyclopentane (283 mg, 1 .35 mmol) in DMF (2 ml_) was added K2CO3 (310 mg, 2.2 mmol). The reaction was stirred at 60 C for 4 hours and then cooled to RT. The mixture was diluted with DCM (20 ml_) and washed with water (2×5 ml_). The organic layer was dried over Na2SO4 and evaporated. The crude product was washed with MeOH (2 ml_) to give 7-(cyclopentylmethyl)-3-propyl- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one 120 mg (41 %) . 1H NMR (CDCI3, 400 MHz TMS): delta 6.91 (d, J=5.6 Hz, 1 H), 6.66 (d, J=5.6 Hz, 1 H), 3.89 (d, J=8.0 Hz, 2H), 2.94 (t, J=7.6 Hz, 2H), 2.37-2.31 (m, 1 H), 1 .92-1 .86 (m, 2H), 1 .73-1 .68 (m, 4H), 1 .63-1 .56 (m, 2H), 1 .32-1 .27 (m, 2H), 1 .04 (t, J=7.4 Hz, 3H). LCMS (MH+): m/z = 261 .1 , tR (minutes, Method 3) = 2.41

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary