Tag: M.W=200-300

Reference of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 mixture of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol), cyclopropylboronic acid (843 mg, 9.8 mmol), Pd(dppf)Cl2 (359 mg, 0.49 mmol) and Na2C03 (1.56 g, 14.7 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was stirred at 90 C under N2 for 48 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6-chloro-8-cyclopropyl-2- methylimidazo[l,2-b]pyridazine (405 mg, 40%). MS m/z 208.0, 210.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
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Related Products of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

5-Bromo-3-chloro-1 ,2-diaminobenzene (4.6 g; 20 mmol; 1 eq.) is dissolved in EtOH (200 mL) and 2,3-dixydroxy-1 ,4-dioxane (2.5 g, 20 mmol; 1 eq.) is added. The mixture is stirred for 4 h at room temperature and a second portion of 2,3-dihydroxy-1 ,4-dioxane (1.3 g; 10 mmol; 0.5 eq.) is added. After stirring for 24 h at room temperature, the reaction mixture is concentrated and the residue is purified by FCC (EtOAc gradient in hexane) to provide 7- bromo-5-chloroquinoxaline as a beige solid (4.7 g; yield: 92%; UPLC purity: 98%).

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
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Electric Literature of 81067-38-1, A common heterocyclic compound, 81067-38-1, name is 1-Bromo-2,3,5-trichlorobenzene, molecular formula is C6H2BrCl3, 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.

2. 2,3,5-Trichlorobenzeneboronic Acid A solution of 2,3,5-trichlorobromobenzene (8.60 g, 0.033 mole) in dry ether (33 ml) and bromoethane (4.73 ml, 7.31 g, 0.067 mole) was added dropwise to a suspension of magnesium turnings (2.809, 0.12 mole) in dry ether (21.50 ml) at room temperature. The mixture was refluxed for 0.50 hr and cooled to room temperature. The mixture was then added dropwise under nitrogen to a solution of trimethylborate (5.16 ml, 5.16 g, 0.05 mole) in dry ether (8.60 ml) maintaining the temperature below -60 C. This was warmed to room temperature overnight, then cooled in an ice-bath and treated with 2M hydrochloric acid (10 ml). The ether layer was separated, washed with water (2*20 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was triturated with 40-60 C. petroleum ether, filtered and dried in vacuo. Yield 4.57 g (61%), M.p. 257-260 C.

The synthetic route of 81067-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome, Inc.; US6255307; (2001); B1;,
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Related Products of 2162-98-3, 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. 2162-98-3, name is 1,10-Dichlorodecane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine (0.45 g, 2.44 mmol), 1,10-dichlorodecane (0.25 g, 1.2mmol), and sulfolane (2 mL) was heated at 190-200 C for 90 h. The resulting mass was stirred with methanol and filtered. The filtrate was concentrated and chromatographedon an Al2O3 column using a gradient from 1 to 25% ofmethanol in methylene chloride. Fractions containing required product were pooled together and evaporated, andthe resulting off-white solid (31 mg, 4.5%) was further purified by crystallization from a methanol/acetone mixture [Mp 250-258 C (dec). 1H NMR (500 MHz, CDCl3) delta1.27-1.43 (m, 12 H), 1.67-1.76 (m, 4 H), 2.20-2.26 (m, 4H), 2.95 (t, 4 H, J = 7.5 Hz), 3.38 (t, 4 H, J = 7.5 Hz), 3.63(t, 4 H, J = 7.0 Hz), 4.46 (t, 4 H, J = 6.5 Hz),7.72 (t, 2 H, J = 7.0 Hz), 7.98 (t, 2 H, J = 7.5 Hz),8.15 (d, 2 H, J = 9.0 Hz), 8.54 (d with fine splitting, 2 H,J = 8.5 Hz), 8.92 (br s, 4 H, NH2).

The synthetic route of 1,10-Dichlorodecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sharma, Arun K.; Krzeminski, Jacek; Weissig, Volkmar; Hegarty, John P.; Stewart, David B.; Journal of Antibiotics; vol. 71; 8; (2018); p. 713 – 721;,
Chloride – Wikipedia,
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Application of 204930-37-0, 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. 204930-37-0 name is 5-Bromo-1,3-dichloro-2-methylbenzene, 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.

To a solution of 5-bromo-1,3-dichloro-2-methylbenzene (1.4 g, 5.8 mmol) in carbon tetrachloride (20 mL) was added N-bromosuccinimide (2.6 g, 14.6 mmol) followed by benzoyl peroxide (71 mg, 0.3 mmol). The reaction was heated at reflux overnight, then cooled to room temperature and filtered through Celite. The solvent was removed in vacuo and the residue was purified via chromatography (100percent hexanes). This provided the product, 5-bromo-2-(bromomethyl)-1,3-dichlorobenzene. 1H NMR (400 MHz, CDCl3) delta 7.50 (s, 2H), 4.68 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,3-dichloro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13065-93-5, name is N1-(4-Chlorophenyl)benzene-1,4-diamine, belongs to chlorides-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 13065-93-5, category: chlorides-buliding-blocks

[0201] Step 3. To a solution of Compound 8-D (0.4 g, 1.8 mmol) and Compound 8-E(0.31 g, 1.8 mmol) in isopropanol (8 mL) was added p-toluenesulfonic acid (0.36 g, 1.9 mmol). The mixture was sealed and heated in microwave at 120 C for 1 hour. Monitoring by thin layer chromatography (petrol ether: ethyl acetate= 1:1 and Rf at 0.6) showed that Compound 8-E was consumed. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (15 mL x 3). The organic layers were concentrated and the residue was purified by preparative HPLC to give the title compound (38 mg, 1.3%, combined with other 5 batches; purity 79% by HPLC) as a white solid. ?H NMR (400 MHz, DMSO) oe 6.94-6.96 (d, J= 8.4 Hz, 1H), 7.07-7.05 (d, J= 8.4 Hz, 1H), 7.17-7.19 (d, J = 8.8 Hz, 1H), 7.50-7.52 (d, J= 8.4 Hz, 1H), 8.14 (s, 1H), 8.80 (s, 1H), 10.19 (s, 1H). MS:302.9 (M+lj.

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, N1-(4-Chlorophenyl)benzene-1,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROPORE THERAPIES, INC.; WRASIDLO, Wolfgang; STOCKING, Emily, M.; WO2014/26039; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 21402-26-6, name is 4-Bromo-3-chloroaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

The product from example 32 step (ii) (O. 5g) and 4-bromo-3-chloroaniline (0. 38G) were dissolved in toluene (4ML). Ethanol (LML), 2M aqueous sodium carbonate (LML) and PD (PPh3) 4 (0. 115G) were added sequentially and the mixture heated at reflux for 4h. The reaction was cooled, evaporated, dissolved in EtOAc, washed with water and brine, dried (MGS04) and evaporated. The residue was purified by chromatography on silica eluting with 10% EtOAc/isohexane. Yield 0.23g. 1H NMR DMSO-d6 : 8 7.67 (ddd, 1H), 7.4 (d, 1H), 7.27-7. 34 (m, 6H), 7.01 (d, 1H), 6.7 (d, 1H), 6.55 (dd, 1H), 5.47 (s, 2H) 5.18 (s, 2H)

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; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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. COA of Formula: C9H11Cl2N

Step 2: To a suspension of 4-(4-chloiO-6-(2,2?2-trifluoroethoxy)-l,3,5-triazin-2- ylamino)faenzenesulfonamide from step 1 (1 g, 2.61 mmol) in THF (20 mL) was added l-(4-chlorophenyl)cyclopropanamine, HC1 (0.53 g, 2.61 mmol) and iPr2NEt (1.35 mL, 10.4 mmol). The mixture was heated at reflux condition for 16 hours. The solvent was removed under vacuum. The crude product 4-(4-(l -(4- chlorophenyl)cyclopropylamino)-6-(2}2,2-trifiuoroethoxy)-l,3J5-triazm-2- ylamino)benzenesulfonamide was used directly in the next step without further purification. LC-MS (Condition A), MS m/z 514.9 (M+ +H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1009102-44-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); A1;,
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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. 892845-59-9, name is 1-Bromo-2-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3BrClF3O

1-bromo-2-chloro-4-(trifluoromethoxy)benzene (0.25 g, 0.91 mmol) was added to an flame dried 50 mL round-bottomed flask charged with a stir bar containing tetrahydrofuran (4.0 mL). The solution was placed under Ar2, cooled to -78 C. and n-butyllithium in hexanes (1.1 M, 0.83 mL) was added dropwise. The reaction proceeded for 5 min at -78 C. and then was quickly poured over dry ice. The solvents were evaporated in vacuo and the subsequent oil was partitioned between H2O and hexanes. The aqueous was washed with hexanes (3*10 mL) and then the aqueous was acidified with 1N HCl (10 mL). The product was extracted with EtOAc (3*20 mL), washed with brine (3*10 mL), dried over MgSO4, and concentrated in vacuo. 1H NMR (500 MHz, CDCl3-d) delta ppm 8.11 (d, J=8.7 Hz, 1H) 7.39 (d, J=1.7 Hz, 1H) 7.22 (dd, J=8.8, 1.7 Hz, 1H); HPLC Ret: 6.65 min.

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 892845-59-9.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; Larsen, Scott D.; Neubig, Richard; Hutchings, Kim; Kahl, Dylan; Lisabeth, Erika Mathes; (56 pag.)US2019/308947; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 202925-05-1,Some common heterocyclic compound, 202925-05-1, name is 4-Chloro-3,5-dibromotoluene, molecular formula is C7H5Br2Cl, 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 7-10 4-[8-(4-Chloro-3,5-dicyclopropylbenzyl)-2-oxo-l-oxa-3,8-diazaspiro[4.5]dec-3-yl]benzoic acid, TFA saltStep 1. Synthesis of I,3-dibromo-5-(bromomethyI)-2~chlorobenzene To l,3-dibromo-2-chloro-5-methylbenzene (1000 mg, 3.52 mmol) was added NBS (688 mg, 3.87 mmol) and AIBN (57.7 mg, 0.352 mmol). The mixture was stirred at room temperature for 30 minutes and then heated to 80 C overnight. The solution was evaporated and the residue was purified by silica gel chromatography (0-5% EtOAc/heaxnes) to provide the title compound (740 mg) as a clear oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3,5-dibromotoluene, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DUFFY, Joseph, L.; BAO, Jianming; ONDEYKA, Debra, L.; TYAGARAJAN, Sriram; SHAO, Patrick; YE, Feng; KATIPALLY, Revathi; ZWICKER, Aaron; SHERER, Edward, C.; PLOTKIN, Michael A.; MONINGKA, Remond; HUSSIAN, Zahid; WOOD, Harold B.; UJJAINWALLA, Feroze; ROMERO, Anthony; FINKE, Paul; ZANG, Yi; LIU, Weiguo; WO2012/24183; (2012); A1;,
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Chlorides – an overview | ScienceDirect Topics